Di-μ-azido-κ4N1:N1′-bis­({1-[(E)-phen­yl(pyridin-2-yl-κN)methyl­idene]thio­semi­carbazidato-κ2N1,S}copper(II))

Kunnath, R.J.; Prathapachandra Kurup, M.R.; Ng, S.W.

doi:10.1107/S1600536812035751

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1195

doi:10.1107/S1600536812035751

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Di-μ-azido-κ⁴N¹:N^1′-bis({1-[(E)-phenyl(pyridin-2-yl-κN)methylidene]thiosemicarbazidato-κ²N¹,S}copper(II))

Roji J. Kunnath,^a M. R. Prathapachandra Kurup ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 August 2012; accepted 14 August 2012; online 23 August 2012)

In the title compound, [Cu₂(C₁₃H₁₁N₄S)₂(N₃)₂], the Cu^II cation is N,N′,S-chelated by the deprotonated Schiff base ligand and is coordinated by the azide anion, while an N atom from an adjacent azide anion bridges the Cu^II cation at the apical position with a longer Cu—N distance of 2.533 (3) Å, completing the distorted N₄S square-pyramidal coordination geometry. A pair of azide anions bridge the two Cu^II cations, forming a centrosymmetric binuclear molecule. In the crystal, the binuclear molecules are linked by an N—H⋯N hydrogen bond into a ribbon running along the a axis.

Related literature

For the structure of the parent Schiff base, see: Casas et al. (2003 ).

Experimental

Crystal data

[Cu₂(C₁₃H₁₁N₄S)₂(N₃)₂]
M_r = 721.78
Monoclinic, P 2₁ /c
a = 11.2462 (12) Å
b = 7.2344 (10) Å
c = 18.519 (2) Å
β = 96.653 (5)°
V = 1496.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.604, T_max = 0.690
13614 measured reflections
3747 independent reflections
2973 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.134
S = 1.04
3747 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯N2ⁱ	0.87 (1)	2.22 (1)	3.075 (3)	168 (4)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035751/xu5611sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035751/xu5611Isup2.hkl

checkCIF report

Comment top

2-Benzoylpyridine thiosemicarbazone (Casas et al., 2003) is a Schiff base that is capable of N,N',S-chelation to metal ions. The Cu^II atom in [Cu(N₃)(C₁₃H₁₁N₄S)]₂ (Scheme I) is N,N',S-chelated by the deprotonated Schiff base, and it exists in a square pyramidal environment (Fig. 1). Two molecules are disposed about a center-of-inversion and the distance between the copper atom and their apical nitrogen atom of the other azide is 2.533 (3) Å. Adjacent inversion-related pairs of molecules are linked by an N–H···N hydrogen bond to form a ribbon running along the a-axis (Table 1).

Related literature top

For the structure of the parent Schiff base, see: Casas et al. (2003).

Experimental top

The Schiff base ligand by heating 2-benzoylpyridine (0.183 g,1 mmol) and thiosemicarbazide (0.091 g,1 mmol) for 3 h. Copper acetate hydrate (0.199 g,1 mmol) and sodium azide (0.065 g,1 mmol) was added and the solution heated for another 2 h. Dark green colored crystals were obtained from the cool solution.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Cu(N₃)(C₁₃H₁₁N₄S)]₂ at the 570% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Di-µ-azido-κ⁴N¹:N^1'-bis({1-[(E)-phenyl(pyridin- 2-yl-κN)methylidene]thiosemicarbazidato- κ²N¹,S}copper(II)) top

Crystal data top

[Cu₂(C₁₃H₁₁N₄S)₂(N₃)₂]	F(000) = 732
M_r = 721.78	D_x = 1.602 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4663 reflections
a = 11.2462 (12) Å	θ = 3.0–28.3°
b = 7.2344 (10) Å	µ = 1.61 mm⁻¹
c = 18.519 (2) Å	T = 295 K
β = 96.653 (5)°	Prism, dark green
V = 1496.5 (3) Å³	0.35 × 0.30 × 0.25 mm
Z = 2

Data collection top

Bruker Kappa APEXII diffractometer	3747 independent reflections
Radiation source: fine-focus sealed tube	2973 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
T_min = 0.604, T_max = 0.690	k = −9→9
13614 measured reflections	l = −24→24

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0694P)² + 0.1161P] where P = (F_o² + 2F_c²)/3
3747 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.54 e Å⁻³
2 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Cu₂(C₁₃H₁₁N₄S)₂(N₃)₂]	V = 1496.5 (3) Å³
M_r = 721.78	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2462 (12) Å	µ = 1.61 mm⁻¹
b = 7.2344 (10) Å	T = 295 K
c = 18.519 (2) Å	0.35 × 0.30 × 0.25 mm
β = 96.653 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	3747 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2973 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.690	R_int = 0.075
13614 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.54 e Å⁻³
3747 reflections	Δρ_min = −0.66 e Å⁻³
205 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.40816 (2)	0.66511 (5)	0.521018 (15)	0.03737 (14)
S1	0.31362 (6)	0.55753 (11)	0.61376 (3)	0.0469 (2)
N1	0.24572 (17)	0.7151 (3)	0.47503 (10)	0.0345 (4)
N2	0.14750 (19)	0.6402 (3)	0.50005 (12)	0.0408 (5)
N3	0.0841 (2)	0.4802 (5)	0.59265 (14)	0.0617 (8)
H1	0.023 (2)	0.456 (6)	0.5610 (15)	0.074*
H2	0.101 (3)	0.422 (5)	0.6343 (12)	0.074*
N4	0.44641 (18)	0.8236 (3)	0.43679 (11)	0.0377 (5)
N5	0.5749 (2)	0.6199 (4)	0.55657 (12)	0.0468 (6)
N6	0.6113 (2)	0.5803 (4)	0.61823 (13)	0.0487 (6)
N7	0.6497 (3)	0.5408 (5)	0.67545 (14)	0.0721 (9)
C1	0.1174 (2)	0.8573 (3)	0.37564 (12)	0.0340 (5)
C2	0.0861 (3)	0.7823 (4)	0.30754 (14)	0.0454 (6)
H2A	0.1412	0.7109	0.2861	0.054*
C3	−0.0264 (3)	0.8127 (5)	0.27110 (15)	0.0506 (7)
H3	−0.0470	0.7627	0.2251	0.061*
C4	−0.1078 (2)	0.9171 (5)	0.30306 (16)	0.0506 (7)
H4	−0.1848	0.9339	0.2796	0.061*
C5	−0.0752 (3)	0.9963 (5)	0.36967 (17)	0.0556 (8)
H5	−0.1294	1.0707	0.3906	0.067*
C6	0.0364 (2)	0.9669 (4)	0.40563 (14)	0.0456 (6)
H6	0.0576	1.0216	0.4507	0.055*
C7	0.2345 (2)	0.8130 (3)	0.41657 (12)	0.0335 (5)
C8	0.1738 (2)	0.5609 (4)	0.56389 (13)	0.0414 (6)
C9	0.3482 (2)	0.8757 (4)	0.39278 (13)	0.0349 (5)
C10	0.3555 (2)	0.9761 (4)	0.33033 (14)	0.0438 (6)
H10	0.2866	1.0115	0.3010	0.053*
C11	0.4675 (3)	1.0232 (5)	0.31207 (16)	0.0510 (7)
H11	0.4750	1.0910	0.2702	0.061*
C12	0.5668 (3)	0.9688 (5)	0.35637 (17)	0.0546 (7)
H12	0.6428	0.9978	0.3446	0.065*
C13	0.5534 (2)	0.8708 (4)	0.41863 (16)	0.0460 (6)
H13	0.6214	0.8364	0.4490	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03127 (19)	0.0431 (2)	0.0358 (2)	0.00031 (11)	−0.00433 (13)	0.00303 (12)
S1	0.0438 (4)	0.0589 (5)	0.0356 (3)	−0.0033 (3)	−0.0049 (3)	0.0100 (3)
N1	0.0312 (9)	0.0386 (12)	0.0328 (9)	−0.0013 (8)	−0.0002 (7)	0.0049 (8)
N2	0.0332 (10)	0.0478 (14)	0.0404 (11)	−0.0046 (9)	−0.0003 (8)	0.0132 (9)
N3	0.0541 (15)	0.079 (2)	0.0504 (14)	−0.0192 (14)	−0.0032 (11)	0.0287 (14)
N4	0.0325 (10)	0.0390 (13)	0.0410 (11)	−0.0018 (8)	0.0018 (8)	−0.0002 (8)
N5	0.0366 (11)	0.0595 (16)	0.0412 (12)	0.0036 (11)	−0.0092 (9)	0.0006 (11)
N6	0.0408 (11)	0.0518 (16)	0.0499 (13)	0.0046 (10)	−0.0099 (10)	−0.0094 (11)
N7	0.081 (2)	0.083 (2)	0.0462 (14)	0.0153 (16)	−0.0196 (13)	−0.0044 (14)
C1	0.0341 (11)	0.0368 (14)	0.0308 (11)	−0.0008 (9)	0.0026 (9)	0.0077 (9)
C2	0.0456 (14)	0.0489 (17)	0.0402 (13)	0.0035 (12)	−0.0013 (10)	−0.0058 (12)
C3	0.0508 (16)	0.061 (2)	0.0370 (13)	−0.0032 (13)	−0.0064 (11)	0.0039 (12)
C4	0.0367 (13)	0.060 (2)	0.0527 (15)	0.0040 (12)	−0.0052 (11)	0.0219 (14)
C5	0.0421 (14)	0.065 (2)	0.0608 (17)	0.0200 (14)	0.0120 (12)	0.0086 (15)
C6	0.0455 (14)	0.0547 (18)	0.0368 (12)	0.0050 (12)	0.0057 (10)	0.0012 (11)
C7	0.0319 (11)	0.0343 (14)	0.0337 (11)	0.0022 (9)	0.0012 (9)	0.0002 (9)
C8	0.0409 (13)	0.0449 (17)	0.0370 (12)	−0.0025 (11)	−0.0006 (10)	0.0075 (10)
C9	0.0348 (11)	0.0332 (13)	0.0369 (11)	−0.0001 (10)	0.0050 (9)	−0.0004 (9)
C10	0.0446 (14)	0.0453 (17)	0.0418 (13)	−0.0020 (11)	0.0062 (11)	0.0050 (11)
C11	0.0551 (17)	0.0497 (18)	0.0508 (15)	−0.0051 (13)	0.0171 (13)	0.0057 (13)
C12	0.0425 (14)	0.055 (2)	0.0695 (19)	−0.0090 (13)	0.0208 (13)	−0.0018 (15)
C13	0.0336 (12)	0.0482 (17)	0.0557 (16)	−0.0032 (11)	0.0034 (11)	−0.0029 (12)

Geometric parameters (Å, º) top

Cu1—N5	1.942 (2)	C2—C3	1.381 (4)
Cu1—N1	1.9578 (19)	C2—H2A	0.9300
Cu1—N4	2.022 (2)	C3—C4	1.373 (4)
Cu1—S1	2.2603 (8)	C3—H3	0.9300
Cu1—N5ⁱ	2.533 (3)	C4—C5	1.371 (5)
S1—C8	1.729 (3)	C4—H4	0.9300
N1—C7	1.287 (3)	C5—C6	1.368 (4)
N1—N2	1.359 (3)	C5—H5	0.9300
N2—C8	1.316 (3)	C6—H6	0.9300
N3—C8	1.329 (4)	C7—C9	1.472 (3)
N3—H1	0.872 (10)	C9—C10	1.376 (3)
N3—H2	0.879 (10)	C10—C11	1.384 (4)
N4—C13	1.331 (3)	C10—H10	0.9300
N4—C9	1.348 (3)	C11—C12	1.364 (4)
N5—N6	1.202 (3)	C11—H11	0.9300
N6—N7	1.134 (3)	C12—C13	1.377 (4)
C1—C6	1.372 (4)	C12—H12	0.9300
C1—C2	1.380 (4)	C13—H13	0.9300
C1—C7	1.477 (3)

N5—Cu1—N1	173.91 (9)	C2—C3—H3	120.1
N5—Cu1—N4	94.22 (9)	C5—C4—C3	119.7 (2)
N1—Cu1—N4	80.26 (8)	C5—C4—H4	120.1
N5—Cu1—S1	101.84 (7)	C3—C4—H4	120.1
N1—Cu1—S1	84.08 (6)	C6—C5—C4	120.5 (3)
N4—Cu1—S1	160.44 (7)	C6—C5—H5	119.7
N5—Cu1—N5ⁱ	85.54 (9)	C4—C5—H5	119.7
N1—Cu1—N5ⁱ	91.79 (8)	C5—C6—C1	120.5 (3)
N4—Cu1—N5ⁱ	89.28 (8)	C5—C6—H6	119.8
S1—Cu1—N5ⁱ	102.92 (6)	C1—C6—H6	119.8
C8—S1—Cu1	93.90 (9)	N1—C7—C9	114.7 (2)
C7—N1—N2	120.1 (2)	N1—C7—C1	123.1 (2)
C7—N1—Cu1	117.58 (17)	C9—C7—C1	122.3 (2)
N2—N1—Cu1	122.15 (15)	N2—C8—N3	116.7 (2)
C8—N2—N1	111.9 (2)	N2—C8—S1	125.6 (2)
C8—N3—H1	114 (2)	N3—C8—S1	117.71 (19)
C8—N3—H2	118 (3)	N4—C9—C10	122.1 (2)
H1—N3—H2	124 (4)	N4—C9—C7	114.3 (2)
C13—N4—C9	118.5 (2)	C10—C9—C7	123.6 (2)
C13—N4—Cu1	128.30 (19)	C9—C10—C11	118.7 (3)
C9—N4—Cu1	113.11 (16)	C9—C10—H10	120.7
N6—N5—Cu1	124.8 (2)	C11—C10—H10	120.7
N7—N6—N5	177.3 (3)	C12—C11—C10	119.1 (3)
C6—C1—C2	119.1 (2)	C12—C11—H11	120.4
C6—C1—C7	120.8 (2)	C10—C11—H11	120.4
C2—C1—C7	120.1 (2)	C11—C12—C13	119.4 (3)
C1—C2—C3	120.4 (3)	C11—C12—H12	120.3
C1—C2—H2A	119.8	C13—C12—H12	120.3
C3—C2—H2A	119.8	N4—C13—C12	122.2 (3)
C4—C3—C2	119.8 (3)	N4—C13—H13	118.9
C4—C3—H3	120.1	C12—C13—H13	118.9

N5—Cu1—S1—C8	−167.21 (13)	C2—C1—C6—C5	2.2 (4)
N1—Cu1—S1—C8	11.35 (12)	C7—C1—C6—C5	−175.2 (3)
N4—Cu1—S1—C8	48.2 (2)	N2—N1—C7—C9	−176.1 (2)
N5ⁱ—Cu1—S1—C8	−79.13 (11)	Cu1—N1—C7—C9	−0.5 (3)
N4—Cu1—N1—C7	1.37 (19)	N2—N1—C7—C1	3.0 (4)
S1—Cu1—N1—C7	169.6 (2)	Cu1—N1—C7—C1	178.59 (18)
N5ⁱ—Cu1—N1—C7	−87.6 (2)	C6—C1—C7—N1	65.7 (4)
N4—Cu1—N1—N2	176.9 (2)	C2—C1—C7—N1	−111.7 (3)
S1—Cu1—N1—N2	−14.88 (19)	C6—C1—C7—C9	−115.3 (3)
N5ⁱ—Cu1—N1—N2	87.9 (2)	C2—C1—C7—C9	67.3 (3)
C7—N1—N2—C8	−173.5 (2)	N1—N2—C8—N3	−178.8 (3)
Cu1—N1—N2—C8	11.1 (3)	N1—N2—C8—S1	2.6 (4)
N5—Cu1—N4—C13	−0.4 (2)	Cu1—S1—C8—N2	−11.5 (3)
N1—Cu1—N4—C13	−177.8 (3)	Cu1—S1—C8—N3	170.0 (3)
S1—Cu1—N4—C13	144.9 (2)	C13—N4—C9—C10	−0.3 (4)
N5ⁱ—Cu1—N4—C13	−85.9 (2)	Cu1—N4—C9—C10	−176.6 (2)
N5—Cu1—N4—C9	175.44 (18)	C13—N4—C9—C7	178.6 (2)
N1—Cu1—N4—C9	−1.97 (17)	Cu1—N4—C9—C7	2.2 (3)
S1—Cu1—N4—C9	−39.2 (3)	N1—C7—C9—N4	−1.2 (3)
N5ⁱ—Cu1—N4—C9	89.97 (18)	C1—C7—C9—N4	179.7 (2)
N4—Cu1—N5—N6	155.8 (3)	N1—C7—C9—C10	177.6 (3)
S1—Cu1—N5—N6	−13.0 (3)	C1—C7—C9—C10	−1.5 (4)
N5ⁱ—Cu1—N5—N6	−115.3 (3)	N4—C9—C10—C11	0.6 (4)
C6—C1—C2—C3	−2.0 (4)	C7—C9—C10—C11	−178.1 (3)
C7—C1—C2—C3	175.5 (3)	C9—C10—C11—C12	0.0 (5)
C1—C2—C3—C4	−0.5 (5)	C10—C11—C12—C13	−0.9 (5)
C2—C3—C4—C5	2.6 (5)	C9—N4—C13—C12	−0.7 (4)
C3—C4—C5—C6	−2.3 (5)	Cu1—N4—C13—C12	175.0 (2)
C4—C5—C6—C1	−0.1 (5)	C11—C12—C13—N4	1.3 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N2ⁱⁱ	0.87 (1)	2.22 (1)	3.075 (3)	168 (4)

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₃H₁₁N₄S)₂(N₃)₂]
M_r	721.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.2462 (12), 7.2344 (10), 18.519 (2)
β (°)	96.653 (5)
V (Å³)	1496.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.604, 0.690
No. of measured, independent and observed [I > 2σ(I)] reflections	13614, 3747, 2973
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.134, 1.04
No. of reflections	3747
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.66

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N2ⁱ	0.87 (1)	2.22 (1)	3.075 (3)	168 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

RJK thanks the University Grants Commission (India) for a Junior Research Fellowship. We thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, for the diffraction measurements. We also thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

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