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The asymmetric unit of the title compound, [Cu2(NCS)2(C10H13N2O)2], contains one-half of the centrosymmetric dinuclear complex, which exhibits a Cu...Cu separation of 3.255 (2) Å. In the complex, each CuII ion is penta­coordinated in a square-pyramidal geometry. The basal plane is formed by one phenol O [Cu—O = 1.910 (4) Å], one imine N [Cu—N = 1.922 (5) Å] and one amine N [Cu—N = 2.041 (5) Å] atoms from the Schiff base ligand, and by the N atom [Cu—N = 1.940 (6) Å] from a thio­cyanate ligand. The apical position is occupied by the N atom [Cu—N = 2.768 (6) Å] of another thio­cyanate ligand. There are intramolecular N—H...O hydrogen bonds linking the two ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047022/cv2307sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047022/cv2307Isup2.hkl
Contains datablock I

CCDC reference: 663663

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.064
  • wR factor = 0.160
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... S PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.22 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

In continuation of our study of copper complexes with Shiff base ligands (Wei, 2005a,b; Wei & Wang, 2006), we report here the crystal structure of the title compound- a new dinuclear copper(II) complex (Fig. 1).

Each Cu atom in the complex is pentacoordinate in a square pyramidal geometry, with one phenolic O, one imine N, and one amine N atoms of one Schiff base ligand, and with one N atom of a thiocyanate ligand defining the basal plane, and with one N atom of another thiocyanate ligand occupying the apical position. The thiocyanate ligands adopt end-on coordination mode, with the Cu···Cu distance of 3.255 (2) Å. The coordinate bond lengths and angles are comparable with those observed in other Schiff base copper(II) complexes (Diao, Shu et al., 2007; Diao & Li, 2007).

Related literature top

For related structures, see: Diao et al. (2007); Diao & Li (2007); Wei (2005a,b); Wei & Wang (2006).

Experimental top

Salicyaldehyde (1.0 mmol, 122.1 mg), N-methylethane-1,2-diamine (1.0 mmol, 74.0 mg), NH4NCS (1.0 mmol, 7.6 mg) and Cu(CH3COO)2.H2O (1.0 mmol, 199.1 mg) were dissolved in a methanol solution (150 ml). The mixture was refluxed at 340 K for about 1 h to give a clear blue solution. After keeping the cooled resulting solution in dark for five days, blue needle-shaped crystals were formed.

Refinement top

Atom H2 attached to N2 was located from a difference Fourier map and refined isotropically, with N–H distance restrained to 0.90 (3) Å. Other H atoms were placed geometrically, with C–H distances in the range 0.93–0.97 Å, and with Uiso(H) set to 1.2Ueq(C) and 1.5Ueq(methyl C).

Structure description top

In continuation of our study of copper complexes with Shiff base ligands (Wei, 2005a,b; Wei & Wang, 2006), we report here the crystal structure of the title compound- a new dinuclear copper(II) complex (Fig. 1).

Each Cu atom in the complex is pentacoordinate in a square pyramidal geometry, with one phenolic O, one imine N, and one amine N atoms of one Schiff base ligand, and with one N atom of a thiocyanate ligand defining the basal plane, and with one N atom of another thiocyanate ligand occupying the apical position. The thiocyanate ligands adopt end-on coordination mode, with the Cu···Cu distance of 3.255 (2) Å. The coordinate bond lengths and angles are comparable with those observed in other Schiff base copper(II) complexes (Diao, Shu et al., 2007; Diao & Li, 2007).

For related structures, see: Diao et al. (2007); Diao & Li (2007); Wei (2005a,b); Wei & Wang (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level. Unlabelled atoms are related with labelled ones by symmetry code (-x + 2, -y, -z + 1).
Di-µ-thiocyanato-κ4N:N-bis({2-[2- (methylamino)ethyliminomethyl]phenolato}copper(II)) top
Crystal data top
[Cu2(NCS)2(C10H13N2O)2]F(000) = 612
Mr = 597.69Dx = 1.602 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.3305 (19) ÅCell parameters from 944 reflections
b = 16.982 (4) Åθ = 2.3–24.9°
c = 9.137 (2) ŵ = 1.92 mm1
β = 106.562 (3)°T = 298 K
V = 1239.0 (5) Å3Needle, blue
Z = 20.20 × 0.07 × 0.06 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2431 independent reflections
Radiation source: fine-focus sealed tube1510 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.700, Tmax = 0.894k = 2020
9340 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0643P)2 + 0.4135P]
where P = (Fo2 + 2Fc2)/3
2431 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.45 e Å3
1 restraintΔρmin = 0.67 e Å3
Crystal data top
[Cu2(NCS)2(C10H13N2O)2]V = 1239.0 (5) Å3
Mr = 597.69Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.3305 (19) ŵ = 1.92 mm1
b = 16.982 (4) ÅT = 298 K
c = 9.137 (2) Å0.20 × 0.07 × 0.06 mm
β = 106.562 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2431 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1510 reflections with I > 2σ(I)
Tmin = 0.700, Tmax = 0.894Rint = 0.087
9340 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0641 restraint
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.45 e Å3
2431 reflectionsΔρmin = 0.67 e Å3
158 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.96892 (9)0.04411 (4)0.33613 (8)0.0410 (3)
S11.4907 (3)0.09746 (15)0.6792 (3)0.1066 (10)
O11.0498 (5)0.0513 (2)0.2719 (4)0.0443 (10)
N10.7859 (6)0.0530 (3)0.1529 (5)0.0398 (12)
N20.8447 (7)0.1282 (3)0.4207 (5)0.0463 (13)
N31.1753 (7)0.0566 (3)0.4992 (6)0.0558 (15)
C10.8475 (8)0.0616 (3)0.0253 (7)0.0412 (14)
C20.9862 (7)0.0881 (3)0.1430 (6)0.0372 (14)
C31.0614 (9)0.1608 (4)0.1219 (8)0.0530 (17)
H31.14950.18080.20000.064*
C41.0052 (10)0.2015 (4)0.0123 (9)0.066 (2)
H41.05560.24910.02370.079*
C50.8739 (10)0.1731 (5)0.1324 (9)0.070 (2)
H50.83930.20080.22380.084*
C60.7964 (9)0.1042 (4)0.1144 (7)0.0562 (18)
H60.70930.08510.19440.067*
C70.7571 (7)0.0073 (3)0.0369 (6)0.0406 (14)
H70.66870.02070.04750.049*
C80.6778 (8)0.1198 (4)0.1574 (7)0.0503 (16)
H8A0.56650.11060.08960.060*
H8B0.72240.16720.12430.060*
C90.6698 (8)0.1295 (4)0.3187 (7)0.0554 (17)
H9A0.61630.17910.32950.066*
H9B0.60540.08710.34510.066*
C100.9218 (9)0.2060 (4)0.4491 (8)0.072 (2)
H10A0.93400.22720.35540.108*
H10B1.02990.20180.52240.108*
H10C0.85210.24030.48810.108*
C111.3052 (9)0.0744 (4)0.5740 (7)0.0510 (17)
H20.841 (9)0.110 (4)0.512 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0387 (4)0.0473 (5)0.0355 (4)0.0051 (4)0.0082 (3)0.0031 (4)
S10.0748 (16)0.1044 (19)0.1027 (17)0.0400 (14)0.0359 (13)0.0478 (15)
O10.050 (3)0.049 (3)0.033 (2)0.011 (2)0.0107 (19)0.0028 (19)
N10.034 (3)0.045 (3)0.041 (3)0.008 (2)0.011 (2)0.010 (2)
N20.054 (3)0.044 (3)0.042 (3)0.003 (3)0.017 (3)0.010 (2)
N30.047 (3)0.072 (4)0.047 (3)0.007 (3)0.011 (3)0.007 (3)
C10.040 (4)0.044 (4)0.046 (4)0.014 (3)0.021 (3)0.006 (3)
C20.041 (4)0.045 (4)0.032 (3)0.004 (3)0.020 (3)0.006 (3)
C30.069 (5)0.042 (4)0.057 (4)0.006 (3)0.034 (4)0.003 (3)
C40.085 (6)0.049 (4)0.078 (5)0.008 (4)0.048 (5)0.013 (4)
C50.087 (6)0.076 (5)0.064 (5)0.036 (5)0.050 (5)0.037 (4)
C60.059 (4)0.077 (5)0.039 (4)0.017 (4)0.024 (3)0.009 (4)
C70.042 (4)0.050 (4)0.026 (3)0.003 (3)0.004 (3)0.002 (3)
C80.048 (4)0.056 (4)0.044 (4)0.010 (3)0.009 (3)0.006 (3)
C90.042 (4)0.059 (4)0.067 (5)0.011 (3)0.018 (3)0.003 (4)
C100.078 (6)0.058 (5)0.084 (5)0.001 (4)0.032 (4)0.016 (4)
C110.050 (4)0.056 (4)0.041 (4)0.001 (3)0.005 (3)0.008 (3)
Geometric parameters (Å, º) top
Cu1—O11.910 (4)C3—C41.369 (9)
Cu1—N11.922 (5)C3—H30.9300
Cu1—N31.940 (6)C4—C51.396 (10)
Cu1—N22.041 (5)C4—H40.9300
S1—C111.617 (7)C5—C61.368 (10)
O1—C21.305 (6)C5—H50.9300
N1—C71.280 (7)C6—H60.9300
N1—C81.457 (7)C7—H70.9300
N2—C101.459 (8)C8—C91.503 (8)
N2—C91.490 (8)C8—H8A0.9700
N2—H20.90 (4)C8—H8B0.9700
N3—C111.144 (8)C9—H9A0.9700
C1—C21.410 (8)C9—H9B0.9700
C1—C71.411 (8)C10—H10A0.9600
C1—C61.423 (8)C10—H10B0.9600
C2—C31.422 (8)C10—H10C0.9600
O1—Cu1—N193.47 (18)C6—C5—C4119.5 (6)
O1—Cu1—N390.91 (19)C6—C5—H5120.3
N1—Cu1—N3165.9 (2)C4—C5—H5120.3
O1—Cu1—N2166.3 (2)C5—C6—C1120.8 (7)
N1—Cu1—N285.0 (2)C5—C6—H6119.6
N3—Cu1—N293.8 (2)C1—C6—H6119.6
C2—O1—Cu1126.6 (4)N1—C7—C1125.9 (5)
C7—N1—C8121.6 (5)N1—C7—H7117.0
C7—N1—Cu1126.0 (4)C1—C7—H7117.0
C8—N1—Cu1112.3 (4)N1—C8—C9108.3 (5)
C10—N2—C9113.6 (5)N1—C8—H8A110.0
C10—N2—Cu1117.1 (4)C9—C8—H8A110.0
C9—N2—Cu1106.5 (4)N1—C8—H8B110.0
C10—N2—H2106 (5)C9—C8—H8B110.0
C9—N2—H2107 (5)H8A—C8—H8B108.4
Cu1—N2—H2105 (5)N2—C9—C8107.7 (5)
C11—N3—Cu1165.6 (6)N2—C9—H9A110.2
C2—C1—C7123.1 (5)C8—C9—H9A110.2
C2—C1—C6119.5 (6)N2—C9—H9B110.2
C7—C1—C6117.4 (6)C8—C9—H9B110.2
O1—C2—C1124.7 (5)H9A—C9—H9B108.5
O1—C2—C3117.2 (5)N2—C10—H10A109.5
C1—C2—C3118.1 (5)N2—C10—H10B109.5
C4—C3—C2120.6 (6)H10A—C10—H10B109.5
C4—C3—H3119.7N2—C10—H10C109.5
C2—C3—H3119.7H10A—C10—H10C109.5
C3—C4—C5121.4 (7)H10B—C10—H10C109.5
C3—C4—H4119.3N3—C11—S1178.6 (7)
C5—C4—H4119.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (4)2.17 (3)2.993 (6)153 (6)
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula[Cu2(NCS)2(C10H13N2O)2]
Mr597.69
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)8.3305 (19), 16.982 (4), 9.137 (2)
β (°) 106.562 (3)
V3)1239.0 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.92
Crystal size (mm)0.20 × 0.07 × 0.06
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.700, 0.894
No. of measured, independent and
observed [I > 2σ(I)] reflections
9340, 2431, 1510
Rint0.087
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.160, 1.06
No. of reflections2431
No. of parameters158
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.67

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (4)2.17 (3)2.993 (6)153 (6)
Symmetry code: (i) x+2, y, z+1.
 

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