metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[μ-4-Benzoyl-1-(1-oxido-2-naphthyl­carbon­yl)thio­semicarbazidato(4−)]bis­­[pyridine­copper(II)]

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 12 September 2009; accepted 7 October 2009; online 17 October 2009)

In the title dinuclear complex, [Cu2(C19H11N3O3S)(C5H5N)2], the two CuII centers have different coordination environments, viz. N2OS and N2O2, each exhibiting a distorted square-planar geometry. ππ inter­actions between the aromatic rings of neighbouring complexes [centroid–centroid distance = 3.856 (5) Å] link pairs of mol­ecules into centrosymmetric dimers, which are further packed into stacks along the b axis with relatively short Cu⋯Cu separations of 3.482 (1) Å. Weak inter­molecular C—H⋯N hydrogen bonds help to consolidate the crystal packing.

Related literature

For details of the synthesis, see: Chen et al. (2007[Chen, Y.-T., Dou, J.-M., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2007). Acta Cryst. E63, m2503-m2504.]). For pharmacological properties of complexes of acyl­thio­semicarbazides, see: Wei et al. (1995[Wei, T. B., Chen, J. C., Yang, S. Y. & Wang, X. C. (1995). Chem. Res. Appl. 7, 194-198.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu2(C19H11N3O3S)(C5H5N)2]

  • Mr = 646.65

  • Monoclinic, P 21 /n

  • a = 12.7621 (14) Å

  • b = 9.2609 (11) Å

  • c = 21.683 (2) Å

  • β = 92.168 (2)°

  • V = 2560.9 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.79 mm−1

  • T = 298 K

  • 0.48 × 0.42 × 0.21 mm

Data collection
  • Bruker SMART 1000 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.481, Tmax = 0.706

  • 12450 measured reflections

  • 4504 independent reflections

  • 2532 reflections with I > 2σ(I)

  • Rint = 0.064

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.161

  • S = 1.00

  • 4504 reflections

  • 361 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C23—H23⋯N3i 0.93 2.53 3.451 (8) 173
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Acylthiosemicarbazides possess strong coordination ability, and their complexes exhibit various biological activities (Wei et al., 1995). Herewith we present the crystal structure of the title compound (I) - new dinuclear complex of naphthalenecarbothiosemicarbazide.

In (I) (Fig. 1), two Cu centers have different coordination environments - N2OS and N2O2, respectively, exhibiting distorted square-planar geometry each. The Cu1 atom is coordinated with one phenolate oxygen, one nitrogen atom of pyridine, one sulfur atom and one hydrazide nitrogen atom, forming five-membered and six-membered chelating rings. The Cu2 atom is coordinated with two carbonyl oxygen atoms, one nitrogen atom of pyridine and one hydrazide nitrogen atom, forming five-membered and six-membered chelating rings too. ππ interactions between the aromatic rings of neighbouring complexes [centroid-to centroid distance = 3.856 (5) Å] link two molecules into centrosymmetric dimers, which are further packed into stacks along b axis with relatively short Cu···Cu separation of 3.482 (1) Å. Weak intermolecular C—H···N hydrogen bonds (Table 1) help to consolidate the crystal packing.

Related literature top

For details of the synthesis, see: Chen et al. (2007). For pharmacological properties of complexes of acylthiosemicarbazides, see: Wei et al. (1995).

Experimental top

1.406 g (10 mmol) of benzoyl chloride was added dropwise to a stirred solution of acetonitrile (50 ml) containing 0.981 g (10 mmol) of potassium thiocyanate. Stirring was continued for 1 h, and the solution was slowly warmed to ambient temperature. Then 1.68 g (10 mmol) of 1-hydroxy-2-naphthalenecarbohydrazide was added to the mixture, with stirring being continued for 5 h. After staying for overnight at refrigerator, the resulting yellow precipitate was filtered and rinsed with diethyl ether, then dried in vacuo, 87% yield. m.p. 225–227 C. The solution of CuNO3(0.04 g, 0.2 mmol) in pyridine(10 ml) was added to the mixture of N-benzoyl-1-hydroxy-2-naphthalenecarbothiosemicarbazide (0.073 g, 0.2 mmol)and sodium methylate(0.0324 g,0.6 mmol)in DMSO(10 ml). A green solution was obtained after refluxing for 3 h. After filtrated,dimethyl ether was slowly diffused into the filtrate, then crystals suitable for X-ray diffraction were obtained after two weeks (m.p. >400 K) (Chen et al. 2007) Elemental analysis calculated for Cu2C29H21N5O3S1: C, 53.64; H, 3.29; N, 9.43. Found (%): C, 53.86; H, 3.27; N, 10.83.

Refinement top

The C-bound H atoms were geometrically positioned (C—H = 0.93 Å), and were refined as riding, with Uiso(H) = 1.2 Ueq(C).

Structure description top

Acylthiosemicarbazides possess strong coordination ability, and their complexes exhibit various biological activities (Wei et al., 1995). Herewith we present the crystal structure of the title compound (I) - new dinuclear complex of naphthalenecarbothiosemicarbazide.

In (I) (Fig. 1), two Cu centers have different coordination environments - N2OS and N2O2, respectively, exhibiting distorted square-planar geometry each. The Cu1 atom is coordinated with one phenolate oxygen, one nitrogen atom of pyridine, one sulfur atom and one hydrazide nitrogen atom, forming five-membered and six-membered chelating rings. The Cu2 atom is coordinated with two carbonyl oxygen atoms, one nitrogen atom of pyridine and one hydrazide nitrogen atom, forming five-membered and six-membered chelating rings too. ππ interactions between the aromatic rings of neighbouring complexes [centroid-to centroid distance = 3.856 (5) Å] link two molecules into centrosymmetric dimers, which are further packed into stacks along b axis with relatively short Cu···Cu separation of 3.482 (1) Å. Weak intermolecular C—H···N hydrogen bonds (Table 1) help to consolidate the crystal packing.

For details of the synthesis, see: Chen et al. (2007). For pharmacological properties of complexes of acylthiosemicarbazides, see: Wei et al. (1995).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[µ-4-Benzoyl-1-(1-oxido-2- naphthylcarbonyl)thiosemicarbazidato(4-)]bis[pyridinecopper(II)] top
Crystal data top
[Cu2(C19H11N3O3S)(C5H5N)2]F(000) = 1312
Mr = 646.65Dx = 1.677 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.7621 (14) ÅCell parameters from 2465 reflections
b = 9.2609 (11) Åθ = 2.4–22.0°
c = 21.683 (2) ŵ = 1.79 mm1
β = 92.168 (2)°T = 298 K
V = 2560.9 (5) Å3Block, green
Z = 40.48 × 0.42 × 0.21 mm
Data collection top
Bruker SMART 1000
diffractometer
4504 independent reflections
Radiation source: fine-focus sealed tube2532 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.481, Tmax = 0.706k = 911
12450 measured reflectionsl = 2225
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0835P)2],
where P = (Fo2 + 2Fc2)/3
4504 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
[Cu2(C19H11N3O3S)(C5H5N)2]V = 2560.9 (5) Å3
Mr = 646.65Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.7621 (14) ŵ = 1.79 mm1
b = 9.2609 (11) ÅT = 298 K
c = 21.683 (2) Å0.48 × 0.42 × 0.21 mm
β = 92.168 (2)°
Data collection top
Bruker SMART 1000
diffractometer
4504 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2532 reflections with I > 2σ(I)
Tmin = 0.481, Tmax = 0.706Rint = 0.064
12450 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.00Δρmax = 0.48 e Å3
4504 reflectionsΔρmin = 0.42 e Å3
361 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.28704 (5)0.20605 (8)1.04261 (3)0.0436 (3)
Cu20.01899 (6)0.36338 (9)0.94557 (3)0.0496 (3)
S10.33285 (12)0.34418 (19)0.96271 (7)0.0508 (5)
N10.1252 (4)0.3405 (5)0.9676 (2)0.0431 (12)
N20.1458 (4)0.2438 (5)1.0159 (2)0.0416 (12)
N30.1971 (4)0.4823 (5)0.8891 (2)0.0418 (12)
N40.4361 (4)0.1750 (5)1.0747 (2)0.0432 (12)
N50.1717 (4)0.3765 (6)0.9268 (2)0.0469 (13)
O10.0142 (3)0.4972 (5)0.88313 (19)0.0540 (12)
O20.0331 (3)0.2309 (5)1.0121 (2)0.0585 (12)
O30.2433 (3)0.0804 (5)1.10597 (19)0.0526 (11)
C10.2062 (5)0.3912 (6)0.9385 (3)0.0415 (15)
C20.1062 (5)0.5270 (7)0.8657 (3)0.0446 (15)
C30.1091 (5)0.6286 (6)0.8125 (3)0.0407 (14)
C40.0197 (5)0.6999 (8)0.7931 (3)0.0595 (19)
H40.04290.68150.81220.071*
C50.0213 (6)0.7982 (8)0.7456 (3)0.067 (2)
H50.03960.84740.73370.080*
C60.1120 (5)0.8241 (7)0.7158 (3)0.0542 (18)
H60.11350.89100.68390.065*
C70.2003 (5)0.7498 (8)0.7339 (3)0.0561 (18)
H70.26200.76520.71340.067*
C80.1998 (5)0.6532 (7)0.7815 (3)0.0527 (17)
H80.26090.60380.79310.063*
C90.0565 (5)0.1886 (7)1.0356 (3)0.0488 (16)
C100.1489 (5)0.0355 (7)1.1163 (3)0.0459 (16)
C110.0576 (5)0.0804 (7)1.0840 (3)0.0466 (16)
C120.0399 (5)0.0174 (8)1.0983 (3)0.066 (2)
H120.09990.04671.07600.079*
C130.0496 (6)0.0831 (9)1.1429 (3)0.070 (2)
H130.11510.12151.15070.084*
C140.0390 (5)0.1290 (7)1.1771 (3)0.0552 (18)
C150.1381 (5)0.0719 (7)1.1649 (3)0.0460 (16)
C160.2265 (5)0.1219 (7)1.1990 (3)0.0511 (17)
H160.29250.08561.19080.061*
C170.2165 (6)0.2236 (8)1.2443 (3)0.0607 (19)
H170.27550.25701.26650.073*
C180.1178 (6)0.2766 (8)1.2570 (3)0.064 (2)
H180.11100.34311.28880.077*
C190.0320 (6)0.2337 (8)1.2244 (3)0.0615 (19)
H190.03280.27331.23290.074*
C200.4648 (6)0.0479 (8)1.0975 (3)0.0620 (19)
H200.41520.02571.09780.074*
C210.5641 (6)0.0195 (9)1.1207 (4)0.075 (2)
H210.58160.07231.13510.090*
C220.6363 (6)0.1260 (9)1.1223 (3)0.071 (2)
H220.70400.10891.13800.085*
C230.6084 (5)0.2589 (8)1.1005 (3)0.0593 (19)
H230.65620.33471.10190.071*
C240.5086 (5)0.2789 (7)1.0765 (3)0.0497 (16)
H240.49050.36931.06060.060*
C250.2383 (5)0.2922 (8)0.9581 (3)0.0553 (18)
H250.21140.23300.98960.066*
C260.3436 (5)0.2916 (8)0.9450 (3)0.060 (2)
H260.38740.23130.96670.072*
C270.3842 (5)0.3799 (9)0.8998 (3)0.063 (2)
H270.45590.38050.89040.075*
C280.3189 (5)0.4669 (9)0.8687 (3)0.065 (2)
H280.34470.52900.83800.078*
C290.2128 (5)0.4602 (8)0.8839 (3)0.0571 (18)
H290.16790.51900.86230.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0386 (4)0.0450 (5)0.0473 (5)0.0080 (4)0.0043 (3)0.0035 (4)
Cu20.0350 (4)0.0602 (6)0.0536 (5)0.0116 (4)0.0012 (4)0.0081 (4)
S10.0370 (9)0.0626 (12)0.0528 (10)0.0031 (8)0.0045 (7)0.0147 (8)
N10.038 (3)0.044 (3)0.047 (3)0.012 (2)0.001 (2)0.008 (2)
N20.039 (3)0.051 (3)0.035 (3)0.010 (2)0.000 (2)0.011 (2)
N30.036 (3)0.046 (3)0.043 (3)0.005 (2)0.000 (2)0.009 (2)
N40.043 (3)0.036 (3)0.050 (3)0.003 (2)0.002 (2)0.005 (2)
N50.038 (3)0.056 (4)0.046 (3)0.006 (3)0.004 (3)0.005 (3)
O10.033 (2)0.065 (3)0.063 (3)0.012 (2)0.001 (2)0.015 (2)
O20.042 (3)0.075 (3)0.059 (3)0.012 (2)0.001 (2)0.017 (2)
O30.038 (2)0.061 (3)0.059 (3)0.009 (2)0.003 (2)0.014 (2)
C10.043 (4)0.038 (4)0.043 (4)0.004 (3)0.000 (3)0.005 (3)
C20.039 (4)0.048 (4)0.047 (4)0.009 (3)0.001 (3)0.004 (3)
C30.038 (3)0.042 (4)0.041 (3)0.006 (3)0.005 (3)0.004 (3)
C40.041 (4)0.080 (5)0.058 (4)0.003 (4)0.006 (3)0.011 (4)
C50.050 (4)0.082 (6)0.069 (5)0.011 (4)0.003 (4)0.019 (4)
C60.060 (5)0.055 (5)0.048 (4)0.010 (4)0.002 (3)0.011 (3)
C70.044 (4)0.068 (5)0.056 (4)0.001 (4)0.007 (3)0.009 (4)
C80.046 (4)0.059 (5)0.053 (4)0.001 (3)0.001 (3)0.006 (3)
C90.042 (4)0.060 (5)0.045 (4)0.012 (3)0.006 (3)0.003 (3)
C100.044 (4)0.052 (4)0.042 (4)0.013 (3)0.003 (3)0.005 (3)
C110.044 (4)0.053 (4)0.043 (4)0.015 (3)0.009 (3)0.005 (3)
C120.044 (4)0.087 (6)0.067 (5)0.021 (4)0.003 (3)0.024 (4)
C130.052 (5)0.091 (6)0.069 (5)0.032 (4)0.015 (4)0.020 (4)
C140.054 (4)0.053 (5)0.059 (4)0.016 (4)0.008 (4)0.010 (3)
C150.060 (4)0.042 (4)0.037 (4)0.007 (3)0.013 (3)0.003 (3)
C160.048 (4)0.056 (5)0.050 (4)0.005 (3)0.008 (3)0.005 (3)
C170.070 (5)0.058 (5)0.054 (4)0.012 (4)0.006 (4)0.002 (4)
C180.079 (6)0.057 (5)0.057 (5)0.000 (4)0.026 (4)0.012 (4)
C190.060 (5)0.061 (5)0.065 (5)0.016 (4)0.011 (4)0.008 (4)
C200.061 (5)0.049 (5)0.075 (5)0.008 (4)0.001 (4)0.008 (4)
C210.067 (5)0.050 (5)0.107 (6)0.010 (4)0.005 (5)0.021 (4)
C220.047 (4)0.079 (6)0.087 (6)0.007 (4)0.005 (4)0.006 (5)
C230.048 (4)0.061 (5)0.068 (5)0.016 (4)0.005 (4)0.006 (4)
C240.045 (4)0.046 (4)0.059 (4)0.003 (3)0.011 (3)0.011 (3)
C250.045 (4)0.072 (5)0.050 (4)0.013 (4)0.011 (3)0.003 (4)
C260.048 (4)0.081 (6)0.053 (4)0.022 (4)0.016 (3)0.011 (4)
C270.039 (4)0.088 (6)0.062 (5)0.014 (4)0.006 (4)0.022 (4)
C280.036 (4)0.093 (6)0.067 (5)0.010 (4)0.005 (4)0.009 (4)
C290.039 (4)0.073 (5)0.060 (4)0.010 (4)0.005 (3)0.002 (4)
Geometric parameters (Å, º) top
Cu1—O31.900 (4)C10—C151.460 (8)
Cu1—N21.905 (5)C11—C121.420 (8)
Cu1—N42.022 (5)C12—C131.350 (9)
Cu1—S12.2487 (17)C12—H120.9300
Cu2—O11.895 (4)C13—C141.395 (9)
Cu2—N11.896 (5)C13—H130.9300
Cu2—O21.908 (4)C14—C151.405 (8)
Cu2—N51.980 (5)C14—C191.415 (9)
S1—C11.736 (6)C15—C161.404 (8)
N1—C11.317 (7)C16—C171.370 (9)
N1—N21.395 (6)C16—H160.9300
N2—C91.333 (7)C17—C181.390 (9)
N3—C21.314 (7)C17—H170.9300
N3—C11.366 (7)C18—C191.341 (9)
N4—C201.322 (8)C18—H180.9300
N4—C241.335 (7)C19—H190.9300
N5—C291.305 (8)C20—C211.372 (9)
N5—C251.355 (8)C20—H200.9300
O1—C21.278 (7)C21—C221.349 (10)
O2—C91.295 (7)C21—H210.9300
O3—C101.302 (7)C22—C231.361 (10)
C2—C31.490 (8)C22—H220.9300
C3—C41.372 (8)C23—C241.371 (8)
C3—C81.379 (8)C23—H230.9300
C4—C51.375 (9)C24—H240.9300
C4—H40.9300C25—C261.363 (9)
C5—C61.368 (9)C25—H250.9300
C5—H50.9300C26—C271.364 (10)
C6—C71.365 (8)C26—H260.9300
C6—H60.9300C27—C281.356 (9)
C7—C81.367 (9)C27—H270.9300
C7—H70.9300C28—C291.384 (8)
C8—H80.9300C28—H280.9300
C9—C111.451 (8)C29—H290.9300
C10—C111.400 (8)
O3—Cu1—N291.84 (18)C11—C10—C15117.6 (5)
O3—Cu1—N487.81 (18)C10—C11—C12119.3 (6)
N2—Cu1—N4176.7 (2)C10—C11—C9123.5 (5)
O3—Cu1—S1175.88 (14)C12—C11—C9117.2 (6)
N2—Cu1—S186.09 (14)C13—C12—C11122.9 (6)
N4—Cu1—S194.46 (14)C13—C12—H12118.5
O1—Cu2—N190.70 (19)C11—C12—H12118.5
O1—Cu2—O2172.29 (18)C12—C13—C14119.8 (6)
N1—Cu2—O281.73 (19)C12—C13—H13120.1
O1—Cu2—N593.3 (2)C14—C13—H13120.1
N1—Cu2—N5176.0 (2)C13—C14—C15120.1 (6)
O2—Cu2—N594.3 (2)C13—C14—C19121.5 (6)
C1—S1—Cu196.3 (2)C15—C14—C19118.4 (6)
C1—N1—N2117.4 (5)C16—C15—C14119.2 (6)
C1—N1—Cu2127.7 (4)C16—C15—C10120.6 (6)
N2—N1—Cu2114.4 (3)C14—C15—C10120.2 (6)
C9—N2—N1110.4 (5)C17—C16—C15120.6 (6)
C9—N2—Cu1129.9 (4)C17—C16—H16119.7
N1—N2—Cu1119.7 (3)C15—C16—H16119.7
C2—N3—C1123.0 (5)C16—C17—C18119.6 (7)
C20—N4—C24116.7 (6)C16—C17—H17120.2
C20—N4—Cu1119.9 (4)C18—C17—H17120.2
C24—N4—Cu1123.3 (4)C19—C18—C17121.2 (7)
C29—N5—C25117.2 (6)C19—C18—H18119.4
C29—N5—Cu2123.2 (4)C17—C18—H18119.4
C25—N5—Cu2119.5 (5)C18—C19—C14120.9 (7)
C2—O1—Cu2125.8 (4)C18—C19—H19119.6
C9—O2—Cu2112.6 (4)C14—C19—H19119.6
C10—O3—Cu1128.3 (4)N4—C20—C21123.1 (7)
N1—C1—N3123.4 (5)N4—C20—H20118.4
N1—C1—S1120.3 (5)C21—C20—H20118.4
N3—C1—S1116.3 (4)C22—C21—C20119.4 (7)
O1—C2—N3128.8 (6)C22—C21—H21120.3
O1—C2—C3114.5 (5)C20—C21—H21120.3
N3—C2—C3116.7 (5)C21—C22—C23118.8 (7)
C4—C3—C8118.3 (6)C21—C22—H22120.6
C4—C3—C2119.8 (6)C23—C22—H22120.6
C8—C3—C2121.8 (6)C22—C23—C24118.8 (7)
C3—C4—C5120.9 (6)C22—C23—H23120.6
C3—C4—H4119.6C24—C23—H23120.6
C5—C4—H4119.6N4—C24—C23123.1 (6)
C6—C5—C4120.5 (7)N4—C24—H24118.4
C6—C5—H5119.8C23—C24—H24118.4
C4—C5—H5119.8N5—C25—C26122.0 (7)
C7—C6—C5118.7 (6)N5—C25—H25119.0
C7—C6—H6120.7C26—C25—H25119.0
C5—C6—H6120.7C25—C26—C27119.5 (7)
C6—C7—C8121.4 (6)C25—C26—H26120.2
C6—C7—H7119.3C27—C26—H26120.2
C8—C7—H7119.3C28—C27—C26119.3 (7)
C7—C8—C3120.3 (6)C28—C27—H27120.3
C7—C8—H8119.9C26—C27—H27120.3
C3—C8—H8119.9C27—C28—C29117.9 (7)
O2—C9—N2120.7 (6)C27—C28—H28121.0
O2—C9—C11118.5 (5)C29—C28—H28121.0
N2—C9—C11120.8 (6)N5—C29—C28124.0 (7)
O3—C10—C11125.2 (6)N5—C29—H29118.0
O3—C10—C15117.1 (6)C28—C29—H29118.0
O3—Cu1—S1—C163.1 (19)C3—C4—C5—C61.7 (11)
N2—Cu1—S1—C13.2 (2)C4—C5—C6—C70.4 (11)
N4—Cu1—S1—C1173.5 (2)C5—C6—C7—C81.3 (11)
O1—Cu2—N1—C18.4 (5)C6—C7—C8—C30.0 (11)
O2—Cu2—N1—C1173.0 (6)C4—C3—C8—C72.0 (10)
N5—Cu2—N1—C1167 (3)C2—C3—C8—C7178.4 (6)
O1—Cu2—N1—N2179.8 (4)Cu2—O2—C9—N24.1 (8)
O2—Cu2—N1—N21.6 (4)Cu2—O2—C9—C11176.1 (5)
N5—Cu2—N1—N25 (3)N1—N2—C9—O22.8 (8)
C1—N1—N2—C9172.4 (5)Cu1—N2—C9—O2178.5 (4)
Cu2—N1—N2—C90.0 (6)N1—N2—C9—C11177.5 (5)
C1—N1—N2—Cu16.5 (7)Cu1—N2—C9—C111.2 (9)
Cu2—N1—N2—Cu1178.9 (2)Cu1—O3—C10—C114.5 (9)
O3—Cu1—N2—C93.5 (6)Cu1—O3—C10—C15174.4 (4)
N4—Cu1—N2—C987 (3)O3—C10—C11—C12177.1 (6)
S1—Cu1—N2—C9172.9 (6)C15—C10—C11—C121.9 (9)
O3—Cu1—N2—N1177.9 (4)O3—C10—C11—C92.4 (11)
N4—Cu1—N2—N194 (3)C15—C10—C11—C9178.6 (6)
S1—Cu1—N2—N15.7 (4)O2—C9—C11—C10174.5 (6)
O3—Cu1—N4—C2034.8 (5)N2—C9—C11—C105.3 (10)
N2—Cu1—N4—C20119 (3)O2—C9—C11—C126.0 (9)
S1—Cu1—N4—C20141.7 (5)N2—C9—C11—C12174.2 (6)
O3—Cu1—N4—C24142.7 (5)C10—C11—C12—C131.3 (12)
N2—Cu1—N4—C2459 (3)C9—C11—C12—C13179.2 (7)
S1—Cu1—N4—C2440.7 (5)C11—C12—C13—C140.0 (12)
O1—Cu2—N5—C290.9 (5)C12—C13—C14—C150.6 (12)
N1—Cu2—N5—C29176 (3)C12—C13—C14—C19179.8 (7)
O2—Cu2—N5—C29177.8 (5)C13—C14—C15—C16178.6 (7)
O1—Cu2—N5—C25177.0 (5)C19—C14—C15—C161.0 (10)
N1—Cu2—N5—C252 (3)C13—C14—C15—C100.1 (10)
O2—Cu2—N5—C254.3 (5)C19—C14—C15—C10179.6 (6)
N1—Cu2—O1—C27.9 (5)O3—C10—C15—C160.9 (9)
O2—Cu2—O1—C218.4 (18)C11—C10—C15—C16179.9 (6)
N5—Cu2—O1—C2171.8 (5)O3—C10—C15—C14177.7 (6)
O1—Cu2—O2—C913.7 (18)C11—C10—C15—C141.3 (9)
N1—Cu2—O2—C93.0 (4)C14—C15—C16—C170.9 (10)
N5—Cu2—O2—C9176.6 (4)C10—C15—C16—C17179.5 (6)
N2—Cu1—O3—C106.4 (5)C15—C16—C17—C180.7 (10)
N4—Cu1—O3—C10176.9 (5)C16—C17—C18—C192.3 (11)
S1—Cu1—O3—C1053 (2)C17—C18—C19—C142.2 (11)
N2—N1—C1—N3177.5 (5)C13—C14—C19—C18179.8 (7)
Cu2—N1—C1—N36.3 (9)C15—C14—C19—C180.5 (11)
N2—N1—C1—S13.0 (8)C24—N4—C20—C211.6 (10)
Cu2—N1—C1—S1174.2 (3)Cu1—N4—C20—C21179.3 (6)
C2—N3—C1—N10.4 (9)N4—C20—C21—C221.9 (12)
C2—N3—C1—S1180.0 (5)C20—C21—C22—C230.3 (12)
Cu1—S1—C1—N11.1 (5)C21—C22—C23—C241.4 (11)
Cu1—S1—C1—N3178.5 (4)C20—N4—C24—C230.2 (9)
Cu2—O1—C2—N35.5 (10)Cu1—N4—C24—C23177.4 (5)
Cu2—O1—C2—C3175.8 (4)C22—C23—C24—N41.7 (10)
C1—N3—C2—O10.1 (10)C29—N5—C25—C261.4 (10)
C1—N3—C2—C3178.8 (5)Cu2—N5—C25—C26176.7 (5)
O1—C2—C3—C410.6 (9)N5—C25—C26—C271.2 (11)
N3—C2—C3—C4168.2 (6)C25—C26—C27—C280.0 (11)
O1—C2—C3—C8168.9 (6)C26—C27—C28—C290.9 (11)
N3—C2—C3—C812.2 (9)C25—N5—C29—C280.4 (10)
C8—C3—C4—C52.9 (10)Cu2—N5—C29—C28177.6 (5)
C2—C3—C4—C5177.5 (6)C27—C28—C29—N50.7 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N3i0.932.533.451 (8)173
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula[Cu2(C19H11N3O3S)(C5H5N)2]
Mr646.65
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)12.7621 (14), 9.2609 (11), 21.683 (2)
β (°) 92.168 (2)
V3)2560.9 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.79
Crystal size (mm)0.48 × 0.42 × 0.21
Data collection
DiffractometerBruker SMART 1000
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.481, 0.706
No. of measured, independent and
observed [I > 2σ(I)] reflections
12450, 4504, 2532
Rint0.064
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.161, 1.00
No. of reflections4504
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.42

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N3i0.932.533.451 (8)172.7
Symmetry code: (i) x+1, y+1, z+2.
 

Acknowledgements

We acknowledge the National Natural Science Foundation of China for financial support (grant No. 20671048).

References

First citationChen, Y.-T., Dou, J.-M., Li, D.-C., Wang, D.-Q. & Zhu, Y.-H. (2007). Acta Cryst. E63, m2503–m2504.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWei, T. B., Chen, J. C., Yang, S. Y. & Wang, X. C. (1995). Chem. Res. Appl. 7, 194–198.  CAS Google Scholar

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