Poly[[μ2-(1Z,N′E)-2-(1,3-benzothia­zol-2-ylsulfan­yl)-N′-(2-oxidobenzyl­idene-κ2O:O)acetohydrazidato-κ2O,N′](pyridine-κN)copper(II)]

Bon, V.V.; Orysyk, S.I.; Pekhnyo, V.I.

doi:10.1107/S160053681004986X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m11

https://doi.org/10.1107/S160053681004986X

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Poly[[μ₂-(1Z,N′E)-2-(1,3-benzothiazol-2-ylsulfanyl)-N′-(2-oxidobenzylidene-κ²O:O)acetohydrazidato-κ²O,N′](pyridine-κN)copper(II)]

Vladimir V. Bon,^a Svitlana I. Orysyk ^a ^* and Vasily I. Pekhnyo ^a

^aInstitute of General and Inorganic Chemistry, NAS Ukraine, Kyiv, Prosp. Palladina 32/34, 03680, Ukraine
^*Correspondence e-mail: orysyk@ionc.kiev.ua

(Received 18 November 2010; accepted 29 November 2010; online 4 December 2010)

In the title compound, [Cu(C₁₆H₁₁N₃O₂S₂)(C₅H₅N)]_n, the Cu^II atom displays a square-pyramidal CuN₂O₃ coordination geometry with strong elongation in the vertex direction. The hydrazone molecule is coordinated to the Cu^II atom in a tridentate manner in the enolic form, creating five- and six-membered chelate metallarings. The pyridine molecule completes the square-planar base of the copper coordination environment. The crystal structure displays zigzag polymeric Cu—O—Cu chains along [001]. Several weak π–π interactions between benzothiazole rings were found in the same direction [centroid–centroid distances = 3.7484 (16), 3.7483 (16), 3.6731 (17) and 3.7649 (17) Å].

Related literature

For general background to the biological activity of hydrazones and their metal complexes, see: Belkheiri et al. (2010 ); Pavan et al. (2010 ). For related structures, see: Luo et al. (2009 ).

Experimental

Crystal data

[Cu(C₁₆H₁₁N₃O₂S₂)(C₅H₅N)]
M_r = 484.04
Orthorhombic, P c c n
a = 21.6256 (5) Å
b = 25.3751 (7) Å
c = 7.1230 (2) Å
V = 3908.76 (18) Å³
Z = 8
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 173 K
0.50 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.550, T_max = 0.923
18118 measured reflections
4003 independent reflections
2903 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.02
4003 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2010 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004986X/rk2250sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004986X/rk2250Isup2.hkl

checkCIF report

Comment top

Structure investigation of hydrazones and their metal complexes attract an interest due to their antioxidant, antimycobacterium, antituberculosis activity and cytotoxicity (Belkheiri et al., 2010; Pavan et al., 2010). In the current paper we report the structure investigation of copper(II) one–dimensional coordination polymer obtained at room temperature.

The asymmetric unit of title compound contains one monomeric chain of the polymer. Copper atom displays square–pyramidal CuN₂O₃ coordination geometry, which is strongly elongated in vertex direction (Fig. 1). Hydrazone molecule is coordinated tridentantly in double deprotonated enolic form creating five– and six–membered chelate metalla rings. The square–planar base of copper coordination polyhedron is complemented by coordinated pyridine molecule. The values of Cu—O and Cu—N bond lengths corresponds to related structures (Luo et al., 2009). The geometry of coordination polyhedron is slightly distorted with adjacent angles in the range 80.71 (9)–99.22 (8)°. The Cu–Cu distance between two copper atoms in the polymeric chain is 3.5640 (5)Å. The valence angles O1–Cu1–O1ⁱ and Cu1–O1–Cu1ⁱⁱ have a same value of 99.22 (8)°. Symmetry codes: (i) 3/2-x, y, -1/2+z; (ii) 3/2-x, y, 1/2+z. The five–membered metalla ring Cu1/O2/C4/N2/N1 has a planar geometry with mean deviation from plane 0.0327Å. Contrariwise, the six–membered ring has an envelope conformation with dihedral angle 22.60 (15)° between Cu1/O1/N1 and O1/C1/C2/C3/N1 planes. The pyridine ring is nearly coplanar to square–planar base of copper coordination environment. The dihedral angle between planes Cu1/O1/O2/N1/N2 and N2/C17—C21 creates 11.02 (14)°. Crystal structure of title compound displays 1D zigzag chains (Cu–O–Cu) along [001] direction (Fig. 2). The adjacent polymeric chains in the crystal structure are connected by weak π–π stacking interactions between benzthiazol and phenyl rings: Cg1···Cg1ⁱⁱⁱ = 3.7484 (16)Å, α = 3°; Cg1···Cg1^iv = 3.7483 (16)Å, α = 3°; Cg1···Cg2ⁱⁱⁱ = 3.6731 (17)Å, α = 2.18 (14)°; Cg1···Cg2^iv = 3.7649 (17)Å, α = 2.18 (14)°; (Cg1 - centroid of the ring S2/N3/C6/C7/C8, Cg2 – centroid of the ring C7–C12, α - dihedral angle between rings. Symmetry codes: (iii) x, 1/2-y, -1/2+z; (iv) x, 1/2-y, 1/2+z.

Related literature top

For general background to the biological activity of hydrazones and their metal complexes, see: Belkheiri et al. (2010); Pavan et al. (2010). For related structures, see: Luo et al. (2009).

Experimental top

Mixture of 20 ml (10 ^-2 mol/L) aqueous solution of copper(II) acetate with 2 ml of pyridine was stirred with 20 ml (10 ^-2 mol/L) ethanolic solution of (E)-2-(benzo[d]thiazol-2-ylthio)-N'-(2-hydroxybenzylidene)acetohydrazide for 1 h. The resulted solution was leaved in dark place for evaporation. After 1 week of stating violet needle–like shape crystals were grown.

Structure description top

For general background to the biological activity of hydrazones and their metal complexes, see: Belkheiri et al. (2010); Pavan et al. (2010). For related structures, see: Luo et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Asymmetric unit of title compound with the atom numbering scheme. Displacement ellipsoids are shown at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Atoms O1ⁱ and Cu1ⁱⁱ generated using symmetry operators: (i) 3/2-x, y, -1/2+z; (ii) 3/2-x, y, 1/2+z.
	Fig. 2. Crystal structure of title compound. View along a axis.

Poly[[µ₂-(1Z,N'E)-2-(1,3-benzothiazol-2-ylsulfanyl)- N'-(2-oxidobenzylidene-κ²O:O)acetohydrazidato- κ²O,N'](pyridine-κN)copper(II)] top

Crystal data top

[Cu(C₁₆H₁₁N₃O₂S₂)(C₅H₅N)]	D_x = 1.645 Mg m⁻³
M_r = 484.04	Melting point: 553 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2558 reflections
a = 21.6256 (5) Å	θ = 2.5–25.0°
b = 25.3751 (7) Å	µ = 1.36 mm⁻¹
c = 7.1230 (2) Å	T = 173 K
V = 3908.76 (18) Å³	Needle, violet
Z = 8	0.50 × 0.08 × 0.06 mm
F(000) = 1976

Data collection top

Bruker APEXII CCD diffractometer	4003 independent reflections
Radiation source: fine-focus sealed tube	2903 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→24
T_min = 0.550, T_max = 0.923	k = −27→31
18118 measured reflections	l = −8→8

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0326P)² + 3.0387P] where P = (F_o² + 2F_c²)/3
4003 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cu(C₁₆H₁₁N₃O₂S₂)(C₅H₅N)]	V = 3908.76 (18) Å³
M_r = 484.04	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 21.6256 (5) Å	µ = 1.36 mm⁻¹
b = 25.3751 (7) Å	T = 173 K
c = 7.1230 (2) Å	0.50 × 0.08 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	4003 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2903 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.923	R_int = 0.055
18118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.02	Δρ_max = 0.38 e Å⁻³
4003 reflections	Δρ_min = −0.33 e Å⁻³
271 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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

	x	y	z	U_iso*/U_eq
Cu1	0.753102 (15)	−0.037321 (13)	0.25835 (5)	0.02055 (11)
S1	0.60090 (3)	0.11100 (3)	−0.02890 (11)	0.02363 (19)
S2	0.53776 (3)	0.21393 (3)	−0.09219 (12)	0.02583 (19)
N1	0.66488 (10)	−0.03048 (9)	0.2427 (3)	0.0187 (5)
N2	0.64317 (10)	0.01688 (9)	0.1648 (4)	0.0200 (5)
N3	0.65432 (11)	0.20772 (9)	−0.0010 (4)	0.0237 (6)
N4	0.84545 (10)	−0.04057 (9)	0.2569 (3)	0.0205 (5)
O1	0.74669 (8)	−0.09381 (8)	0.4338 (3)	0.0256 (5)
O2	0.74812 (8)	0.02913 (7)	0.1199 (3)	0.0251 (5)
C1	0.69993 (13)	−0.12735 (11)	0.4391 (4)	0.0215 (7)
C2	0.64019 (12)	−0.11621 (11)	0.3652 (4)	0.0204 (6)
C3	0.62496 (13)	−0.06622 (11)	0.2816 (4)	0.0207 (7)
H3	0.5828	−0.0593	0.2535	0.025*
C4	0.69083 (12)	0.04394 (11)	0.1080 (4)	0.0194 (6)
C5	0.68084 (12)	0.09696 (11)	0.0213 (5)	0.0246 (7)
H5A	0.7048	0.0990	−0.0969	0.030*
H5B	0.6970	0.1243	0.1074	0.030*
C6	0.60595 (13)	0.17951 (11)	−0.0371 (4)	0.0213 (7)
C7	0.57858 (13)	0.27236 (11)	−0.0661 (4)	0.0222 (7)
C8	0.63975 (13)	0.26134 (11)	−0.0164 (4)	0.0225 (7)
C9	0.68083 (14)	0.30265 (12)	0.0145 (5)	0.0282 (7)
H9	0.7226	0.2958	0.0483	0.034*
C10	0.65983 (14)	0.35356 (12)	−0.0049 (5)	0.0295 (7)
H10	0.6874	0.3821	0.0165	0.035*
C11	0.59887 (14)	0.36401 (12)	−0.0552 (4)	0.0270 (7)
H11	0.5857	0.3995	−0.0680	0.032*
C12	0.55732 (13)	0.32394 (12)	−0.0868 (4)	0.0247 (7)
H12	0.5157	0.3311	−0.1214	0.030*
C13	0.59384 (13)	−0.15471 (12)	0.3780 (5)	0.0291 (8)
H13	0.5541	−0.1475	0.3272	0.035*
C14	0.60447 (15)	−0.20236 (13)	0.4619 (5)	0.0371 (9)
H14	0.5727	−0.2282	0.4666	0.045*
C15	0.66156 (15)	−0.21258 (13)	0.5395 (5)	0.0382 (9)
H15	0.6688	−0.2453	0.6002	0.046*
C16	0.70815 (14)	−0.17588 (12)	0.5300 (5)	0.0313 (8)
H16	0.7469	−0.1836	0.5865	0.038*
C17	0.87917 (12)	−0.00032 (11)	0.1905 (4)	0.0221 (7)
H17	0.8584	0.0293	0.1384	0.027*
C18	0.94300 (13)	−0.00042 (12)	0.1953 (5)	0.0273 (7)
H18	0.9654	0.0287	0.1463	0.033*
C19	0.97394 (14)	−0.04243 (12)	0.2708 (4)	0.0294 (8)
H19	1.0178	−0.0426	0.2788	0.035*
C20	0.93942 (13)	−0.08465 (12)	0.3352 (5)	0.0271 (7)
H20	0.9594	−0.1149	0.3850	0.033*
C21	0.87554 (13)	−0.08248 (12)	0.3266 (4)	0.0239 (7)
H21	0.8522	−0.1116	0.3715	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01372 (17)	0.02016 (19)	0.0278 (2)	−0.00024 (15)	−0.00072 (15)	0.00473 (17)
S1	0.0198 (4)	0.0180 (4)	0.0331 (5)	0.0017 (3)	−0.0009 (3)	0.0003 (3)
S2	0.0218 (4)	0.0219 (4)	0.0337 (5)	0.0014 (3)	−0.0039 (3)	0.0008 (4)
N1	0.0177 (12)	0.0178 (13)	0.0207 (13)	0.0016 (9)	0.0006 (10)	0.0018 (11)
N2	0.0203 (12)	0.0161 (12)	0.0235 (14)	0.0037 (10)	0.0000 (10)	0.0000 (11)
N3	0.0259 (13)	0.0174 (13)	0.0277 (15)	0.0019 (10)	−0.0008 (11)	−0.0019 (12)
N4	0.0175 (12)	0.0225 (13)	0.0214 (14)	0.0007 (10)	−0.0025 (10)	−0.0027 (11)
O1	0.0198 (10)	0.0220 (11)	0.0349 (13)	−0.0019 (8)	−0.0029 (9)	0.0093 (10)
O2	0.0160 (10)	0.0221 (11)	0.0372 (13)	0.0000 (8)	0.0009 (9)	0.0070 (10)
C1	0.0224 (15)	0.0187 (16)	0.0234 (17)	0.0005 (12)	0.0056 (12)	−0.0024 (13)
C2	0.0185 (14)	0.0203 (15)	0.0224 (17)	−0.0019 (12)	0.0039 (12)	−0.0012 (13)
C3	0.0157 (14)	0.0227 (16)	0.0236 (18)	−0.0006 (11)	0.0002 (12)	−0.0032 (13)
C4	0.0208 (14)	0.0191 (15)	0.0183 (15)	0.0019 (12)	0.0000 (12)	−0.0038 (13)
C5	0.0169 (14)	0.0205 (16)	0.036 (2)	0.0009 (11)	0.0047 (13)	0.0048 (14)
C6	0.0222 (15)	0.0196 (16)	0.0221 (17)	0.0031 (12)	0.0010 (12)	−0.0007 (13)
C7	0.0233 (15)	0.0247 (16)	0.0185 (16)	−0.0009 (12)	−0.0004 (12)	0.0002 (14)
C8	0.0224 (15)	0.0205 (17)	0.0247 (17)	0.0035 (11)	0.0011 (13)	−0.0010 (13)
C9	0.0235 (15)	0.0271 (17)	0.034 (2)	−0.0004 (13)	−0.0044 (14)	−0.0029 (15)
C10	0.0317 (17)	0.0223 (17)	0.035 (2)	−0.0039 (13)	0.0018 (14)	−0.0022 (15)
C11	0.0355 (17)	0.0188 (16)	0.0266 (18)	0.0073 (13)	0.0027 (14)	0.0030 (14)
C12	0.0239 (15)	0.0278 (17)	0.0223 (17)	0.0061 (12)	−0.0007 (13)	0.0034 (15)
C13	0.0216 (15)	0.0272 (18)	0.039 (2)	−0.0052 (13)	0.0017 (14)	−0.0050 (16)
C14	0.0324 (18)	0.0233 (18)	0.056 (3)	−0.0090 (14)	0.0096 (16)	0.0027 (17)
C15	0.0387 (19)	0.0196 (17)	0.056 (3)	0.0029 (14)	0.0136 (17)	0.0086 (17)
C16	0.0268 (16)	0.0256 (18)	0.041 (2)	0.0035 (13)	0.0063 (15)	0.0091 (16)
C17	0.0205 (14)	0.0185 (15)	0.0274 (17)	0.0001 (12)	0.0019 (12)	−0.0024 (13)
C18	0.0205 (15)	0.0271 (18)	0.0341 (19)	−0.0011 (13)	0.0030 (13)	−0.0019 (15)
C19	0.0186 (15)	0.040 (2)	0.0300 (19)	0.0041 (13)	0.0023 (13)	−0.0022 (16)
C20	0.0246 (16)	0.0266 (17)	0.0302 (18)	0.0081 (13)	−0.0035 (14)	−0.0011 (15)
C21	0.0245 (15)	0.0236 (17)	0.0236 (17)	0.0014 (13)	0.0012 (13)	−0.0005 (14)

Geometric parameters (Å, º) top

Cu1—O1	1.906 (2)	C7—C12	1.395 (4)
Cu1—N1	1.919 (2)	C7—C8	1.398 (4)
Cu1—O2	1.9566 (19)	C8—C9	1.391 (4)
Cu1—N4	1.999 (2)	C9—C10	1.376 (4)
Cu1—O1ⁱ	2.720 (2)	C9—H9	0.9500
S1—C6	1.743 (3)	C10—C11	1.392 (4)
S1—C5	1.801 (3)	C10—H10	0.9500
S2—C7	1.736 (3)	C11—C12	1.375 (4)
S2—C6	1.758 (3)	C11—H11	0.9500
N1—C3	1.282 (3)	C12—H12	0.9500
N1—N2	1.405 (3)	C13—C14	1.368 (4)
N2—C4	1.303 (3)	C13—H13	0.9500
N3—C6	1.293 (4)	C14—C15	1.377 (5)
N3—C8	1.401 (4)	C14—H14	0.9500
N4—C17	1.341 (4)	C15—C16	1.374 (4)
N4—C21	1.342 (4)	C15—H15	0.9500
O1—C1	1.322 (3)	C16—H16	0.9500
O2—C4	1.298 (3)	C17—C18	1.381 (4)
C1—C16	1.403 (4)	C17—H17	0.9500
C1—C2	1.423 (4)	C18—C19	1.369 (4)
C2—C13	1.403 (4)	C18—H18	0.9500
C2—C3	1.440 (4)	C19—C20	1.384 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.496 (4)	C20—C21	1.384 (4)
C5—H5A	0.9900	C20—H20	0.9500
C5—H5B	0.9900	C21—H21	0.9500

O1—Cu1—N1	91.94 (9)	C12—C7—S2	128.5 (2)
O1—Cu1—O2	167.00 (9)	C8—C7—S2	109.7 (2)
N1—Cu1—O2	80.68 (9)	C9—C8—C7	119.6 (3)
O1—Cu1—N4	92.59 (9)	C9—C8—N3	125.1 (3)
N1—Cu1—N4	175.39 (10)	C7—C8—N3	115.3 (3)
O2—Cu1—N4	95.04 (9)	C10—C9—C8	118.7 (3)
O1—Cu1—O1ⁱ	99.26 (8)	C10—C9—H9	120.6
N1—Cu1—O1ⁱ	89.99 (8)	C8—C9—H9	120.6
O2—Cu1—O1ⁱ	91.47 (8)	C9—C10—C11	121.1 (3)
N4—Cu1—O1ⁱ	88.40 (8)	C9—C10—H10	119.4
C6—S1—C5	98.27 (13)	C11—C10—H10	119.4
C7—S2—C6	88.50 (14)	C12—C11—C10	121.3 (3)
C3—N1—N2	117.7 (2)	C12—C11—H11	119.3
C3—N1—Cu1	126.36 (19)	C10—C11—H11	119.3
N2—N1—Cu1	115.64 (16)	C11—C12—C7	117.4 (3)
C4—N2—N1	108.0 (2)	C11—C12—H12	121.3
C6—N3—C8	109.9 (2)	C7—C12—H12	121.3
C17—N4—C21	118.1 (2)	C14—C13—C2	121.6 (3)
C17—N4—Cu1	120.92 (19)	C14—C13—H13	119.2
C21—N4—Cu1	121.00 (19)	C2—C13—H13	119.2
C1—O1—Cu1	123.95 (19)	C13—C14—C15	119.5 (3)
C4—O2—Cu1	109.57 (17)	C13—C14—H14	120.3
O1—C1—C16	118.8 (3)	C15—C14—H14	120.3
O1—C1—C2	123.8 (3)	C16—C15—C14	120.7 (3)
C16—C1—C2	117.4 (3)	C16—C15—H15	119.7
C13—C2—C1	119.1 (3)	C14—C15—H15	119.7
C13—C2—C3	118.5 (3)	C15—C16—C1	121.7 (3)
C1—C2—C3	122.4 (2)	C15—C16—H16	119.2
N1—C3—C2	123.9 (3)	C1—C16—H16	119.2
N1—C3—H3	118.0	N4—C17—C18	122.2 (3)
C2—C3—H3	118.0	N4—C17—H17	118.9
O2—C4—N2	125.6 (3)	C18—C17—H17	118.9
O2—C4—C5	115.2 (2)	C19—C18—C17	120.0 (3)
N2—C4—C5	119.2 (2)	C19—C18—H18	120.0
C4—C5—S1	113.48 (19)	C17—C18—H18	120.0
C4—C5—H5A	108.9	C18—C19—C20	118.0 (3)
S1—C5—H5A	108.9	C18—C19—H19	121.0
C4—C5—H5B	108.9	C20—C19—H19	121.0
S1—C5—H5B	108.9	C21—C20—C19	119.5 (3)
H5A—C5—H5B	107.7	C21—C20—H20	120.2
N3—C6—S1	126.6 (2)	C19—C20—H20	120.2
N3—C6—S2	116.6 (2)	N4—C21—C20	122.1 (3)
S1—C6—S2	116.77 (16)	N4—C21—H21	118.9
C12—C7—C8	121.8 (3)	C20—C21—H21	118.9

O1—Cu1—N1—C3	−22.8 (3)	C6—S1—C5—C4	158.5 (2)
O2—Cu1—N1—C3	168.0 (3)	C8—N3—C6—S1	−178.0 (2)
O1ⁱ—Cu1—N1—C3	76.5 (2)	C8—N3—C6—S2	−0.3 (3)
O1—Cu1—N1—N2	163.35 (19)	C5—S1—C6—N3	−4.6 (3)
O2—Cu1—N1—N2	−5.89 (19)	C5—S1—C6—S2	177.81 (18)
O1ⁱ—Cu1—N1—N2	−97.38 (19)	C7—S2—C6—N3	0.6 (3)
C3—N1—N2—C4	−169.8 (3)	C7—S2—C6—S1	178.43 (19)
Cu1—N1—N2—C4	4.6 (3)	C6—S2—C7—C12	180.0 (3)
O1—Cu1—N4—C17	−163.1 (2)	C6—S2—C7—C8	−0.6 (2)
O2—Cu1—N4—C17	6.4 (2)	C12—C7—C8—C9	0.3 (5)
O1ⁱ—Cu1—N4—C17	97.7 (2)	S2—C7—C8—C9	−179.1 (2)
O1—Cu1—N4—C21	15.2 (2)	C12—C7—C8—N3	−180.0 (3)
O2—Cu1—N4—C21	−175.4 (2)	S2—C7—C8—N3	0.6 (3)
O1ⁱ—Cu1—N4—C21	−84.0 (2)	C6—N3—C8—C9	179.5 (3)
N1—Cu1—O1—C1	29.8 (2)	C6—N3—C8—C7	−0.2 (4)
O2—Cu1—O1—C1	84.8 (4)	C7—C8—C9—C10	0.0 (5)
N4—Cu1—O1—C1	−149.3 (2)	N3—C8—C9—C10	−179.6 (3)
O1ⁱ—Cu1—O1—C1	−60.5 (2)	C8—C9—C10—C11	−0.3 (5)
O1—Cu1—O2—C4	−50.3 (5)	C9—C10—C11—C12	0.2 (5)
N1—Cu1—O2—C4	5.74 (19)	C10—C11—C12—C7	0.1 (5)
N4—Cu1—O2—C4	−175.98 (19)	C8—C7—C12—C11	−0.4 (5)
O1ⁱ—Cu1—O2—C4	95.49 (19)	S2—C7—C12—C11	178.9 (2)
Cu1—O1—C1—C16	160.3 (2)	C1—C2—C13—C14	0.9 (5)
Cu1—O1—C1—C2	−22.8 (4)	C3—C2—C13—C14	−177.6 (3)
O1—C1—C2—C13	179.9 (3)	C2—C13—C14—C15	1.4 (5)
C16—C1—C2—C13	−3.2 (4)	C13—C14—C15—C16	−1.3 (6)
O1—C1—C2—C3	−1.7 (5)	C14—C15—C16—C1	−1.1 (5)
C16—C1—C2—C3	175.3 (3)	O1—C1—C16—C15	−179.6 (3)
N2—N1—C3—C2	−178.7 (3)	C2—C1—C16—C15	3.3 (5)
Cu1—N1—C3—C2	7.5 (4)	C21—N4—C17—C18	−1.3 (4)
C13—C2—C3—N1	−171.6 (3)	Cu1—N4—C17—C18	177.0 (2)
C1—C2—C3—N1	10.0 (5)	N4—C17—C18—C19	−0.4 (5)
Cu1—O2—C4—N2	−5.4 (4)	C17—C18—C19—C20	2.0 (5)
Cu1—O2—C4—C5	174.4 (2)	C18—C19—C20—C21	−1.9 (5)
N1—N2—C4—O2	0.7 (4)	C17—N4—C21—C20	1.4 (4)
N1—N2—C4—C5	−179.1 (3)	Cu1—N4—C21—C20	−176.9 (2)
O2—C4—C5—S1	170.0 (2)	C19—C20—C21—N4	0.2 (5)
N2—C4—C5—S1	−10.2 (4)

Symmetry code: (i) −x+3/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₁N₃O₂S₂)(C₅H₅N)]
M_r	484.04
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	173
a, b, c (Å)	21.6256 (5), 25.3751 (7), 7.1230 (2)
V (Å³)	3908.76 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.50 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.550, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	18118, 4003, 2903
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.02
No. of reflections	4003
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2010), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Ukrainian National Academy of Sciences for support of this study (project No 20–10).

References

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