Bis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN4)propan-1-one]bis­(thio­cyanato-κN)copper(II)

Cai, H.; Guo, Y.; Li, J.-G.

doi:10.1107/S160053681203108X

metal-organic compounds

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Volume 68| Part 8| August 2012| Page m1115

https://doi.org/10.1107/S160053681203108X

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Bis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1-one]bis(thiocyanato-κN)copper(II)

Hua Cai,^a ^* Ying Guo ^a and Jian-Gang Li ^a

^aCollege of Science, Civil Aviation University of China, Tianjin 300300, People's Republic of China
^*Correspondence e-mail: caihua-1109@163.com

(Received 27 June 2012; accepted 8 July 2012; online 25 July 2012)

The title compound, [Cu(NCS)₂(C₁₁H₁₁N₃O)₂], contains two independent Cu^II atoms. Each Cu^II atom, lying on an inversion center, is coordinated by two N atoms from two NCS⁻ anions and two N atoms from two monodentate 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one ligands in a distorted square-planar geometry. Two S atoms from adjacent molecules occupy the axial positions with long Cu⋯S distances [3.0495 (10) and 3.1045 (9) Å] and complete the overall distorted octahedral coordination sphere. Weak intermolecular C—H⋯O hydrogen bonds are present.

Related literature

For related structures, see: Guo & Cai (2007 ); Yue et al. (2008 ).

Experimental

Crystal data

[Cu(NCS)₂(C₁₁H₁₁N₃O)₂]
M_r = 582.16
Triclinic, $[P \overline 1]$
a = 9.8643 (8) Å
b = 10.1267 (9) Å
c = 14.3538 (12) Å
α = 91.149 (1)°
β = 101.270 (1)°
γ = 110.857 (1)°
V = 1307.75 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.749, T_max = 0.848
7171 measured reflections
4559 independent reflections
3860 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.091
S = 1.08
4559 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.58	3.330 (3)	138

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681203108X/hy2568sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203108X/hy2568Isup2.hkl

checkCIF report

Comment top

Pseudohalide anions N3^-, NCS^- and NCO^- are known as extremely versatile ligands in coordination chemistry because of their multiple bridging modes (Yue et al., 2008). Recently, we have initiated a research program of synthesizing supermolecules based on pseudohalide and flexible ligands that consist of a propanone unit substituted with an imidazole and a phenyl group (Guo & Cai, 2007). To further explore this series, we synthesized the title compound, a new Cu^II complex based on the mixed ligands, thiocyanato and 3-(1H-1,2,4-triazol-1-yl)-1-phenylpropan-1-one (L) which consists of a propanone unit substituted with a triazole and a phenyl group. In the mononuclear title complex (Fig. 1), each Cu^II atom is four-coordinated by two monodentate L ligands and two NCS^- anions, forming a square-planar geometry. Weak intermolecular C—H···O hydrogen bonds are present (Table 1).

Related literature top

For related structures, see: Guo & Cai (2007); Yue et al. (2008).

Experimental top

NH₄SCN (15.2 mg, 0.2 mmol) was added into an acetonitrile solution of L (25.6 mg, 0.1 mmol) with stirring. The acetonitrile solution was added into a solution of CuCl₂.2H₂O (17.0 mg, 0.1 mmol) in acetonitrile/H₂O (10 ml, v/v 1:1) with vigorous stirring for ca 30 min. The reaction solution was filtered and left to stand at room temperature. Blue block crystals of the title compound suitable for X-ray analysis were obtained in 65% yield by slow evaporation of the solvent over a period of 1 week. Analysis, calculated for Cu₂C₄₈H₄₄N₁₆O₄S₄: C 49.52, H 3.81, N 19.25%; found: C 49.45, H 3.89, N 19.36%.

Structure description top

For related structures, see: Guo & Cai (2007); Yue et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the 50% probability ellipsoids. [Symmetry codes: (i) -x, 1-y, -z; (ii) 1-x, -y, -z.]

Bis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1- one]bis(thiocyanato-κN)copper(II) top

Crystal data top

[Cu(NCS)₂(C₁₁H₁₁N₃O)₂]	Z = 2
M_r = 582.16	F(000) = 598
Triclinic, P1	D_x = 1.479 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8643 (8) Å	Cell parameters from 3208 reflections
b = 10.1267 (9) Å	θ = 2.5–27.7°
c = 14.3538 (12) Å	µ = 1.03 mm⁻¹
α = 91.149 (1)°	T = 293 K
β = 101.270 (1)°	Block, blue
γ = 110.857 (1)°	0.28 × 0.24 × 0.16 mm
V = 1307.75 (19) Å³

Data collection top

Bruker APEXII CCD diffractometer	4559 independent reflections
Radiation source: fine-focus sealed tube	3860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.749, T_max = 0.848	k = −10→12
7171 measured reflections	l = −15→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0456P)² + 0.6431P] where P = (F_o² + 2F_c²)/3
4559 reflections	(Δ/σ)_max < 0.001
337 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Cu(NCS)₂(C₁₁H₁₁N₃O)₂]	γ = 110.857 (1)°
M_r = 582.16	V = 1307.75 (19) Å³
Triclinic, P1	Z = 2
a = 9.8643 (8) Å	Mo Kα radiation
b = 10.1267 (9) Å	µ = 1.03 mm⁻¹
c = 14.3538 (12) Å	T = 293 K
α = 91.149 (1)°	0.28 × 0.24 × 0.16 mm
β = 101.270 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4559 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3860 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.848	R_int = 0.013
7171 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	Δρ_max = 0.52 e Å⁻³
4559 reflections	Δρ_min = −0.41 e Å⁻³
337 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

	x	y	z	U_iso*/U_eq
Cu1	0.0000	0.5000	0.0000	0.03694 (13)
Cu2	0.5000	0.0000	0.0000	0.04017 (13)
S1	−0.48000 (8)	0.29758 (9)	0.06142 (7)	0.0654 (2)
S2	0.06035 (8)	−0.21058 (9)	0.10990 (6)	0.0600 (2)
O1	0.4874 (2)	0.1466 (2)	0.35980 (13)	0.0532 (5)
O2	0.87681 (19)	0.03667 (17)	0.56084 (12)	0.0431 (4)
N1	0.0706 (2)	0.4157 (2)	0.11707 (14)	0.0378 (5)
N2	0.0832 (3)	0.3365 (3)	0.26177 (17)	0.0553 (6)
N3	0.1774 (2)	0.3051 (2)	0.21618 (14)	0.0397 (5)
N4	0.6443 (2)	0.0025 (2)	0.11758 (14)	0.0389 (5)
N5	0.7402 (2)	−0.0004 (2)	0.26570 (13)	0.0349 (4)
N6	0.8416 (2)	−0.0119 (3)	0.21731 (15)	0.0511 (6)
N7	−0.1992 (2)	0.4382 (2)	0.02640 (15)	0.0429 (5)
N8	0.3355 (2)	−0.0705 (2)	0.06659 (15)	0.0470 (5)
C1	0.1693 (3)	0.3532 (3)	0.13169 (17)	0.0419 (6)
H1	0.2249	0.3445	0.0882	0.050*
C2	0.0219 (3)	0.4019 (3)	0.19914 (19)	0.0530 (7)
H2	−0.0498	0.4363	0.2103	0.064*
C3	0.2643 (3)	0.2222 (3)	0.25970 (19)	0.0491 (6)
H3A	0.3470	0.2360	0.2291	0.059*
H3B	0.2023	0.1221	0.2499	0.059*
C4	0.3223 (3)	0.2669 (3)	0.36542 (17)	0.0398 (6)
H4A	0.3629	0.3698	0.3756	0.048*
H4B	0.2403	0.2330	0.3976	0.048*
C5	0.4406 (3)	0.2112 (2)	0.40930 (18)	0.0366 (5)
C6	0.5010 (2)	0.2403 (2)	0.51463 (17)	0.0346 (5)
C7	0.4606 (3)	0.3234 (3)	0.57345 (19)	0.0425 (6)
H7	0.3920	0.3636	0.5475	0.051*
C8	0.5217 (3)	0.3471 (3)	0.6704 (2)	0.0482 (6)
H8	0.4929	0.4020	0.7094	0.058*
C9	0.6246 (3)	0.2897 (3)	0.7096 (2)	0.0499 (7)
H9	0.6665	0.3070	0.7747	0.060*
C10	0.6655 (3)	0.2065 (3)	0.6520 (2)	0.0495 (7)
H10	0.7351	0.1677	0.6782	0.059*
C11	0.6040 (3)	0.1811 (3)	0.55633 (18)	0.0421 (6)
H11	0.6310	0.1234	0.5183	0.050*
C12	0.7786 (3)	−0.0106 (3)	0.12931 (18)	0.0486 (7)
H12	0.8219	−0.0181	0.0784	0.058*
C13	0.6252 (3)	0.0090 (3)	0.20563 (16)	0.0372 (5)
H13	0.5429	0.0188	0.2228	0.045*
C14	0.7671 (3)	0.0026 (3)	0.36889 (16)	0.0360 (5)
H14A	0.7983	−0.0751	0.3887	0.043*
H14B	0.6758	−0.0100	0.3897	0.043*
C15	0.8855 (3)	0.1414 (2)	0.41492 (16)	0.0364 (5)
H15A	0.9720	0.1595	0.3874	0.044*
H15B	0.8488	0.2175	0.4011	0.044*
C16	0.9308 (2)	0.1423 (2)	0.52113 (16)	0.0314 (5)
C17	1.0427 (2)	0.2750 (2)	0.57691 (16)	0.0316 (5)
C18	1.0867 (3)	0.2771 (3)	0.67518 (17)	0.0398 (6)
H18	1.0451	0.1966	0.7053	0.048*
C19	1.1913 (3)	0.3976 (3)	0.72822 (19)	0.0496 (7)
H19	1.2211	0.3979	0.7938	0.060*
C20	1.2523 (3)	0.5184 (3)	0.6840 (2)	0.0528 (7)
H20	1.3223	0.6000	0.7201	0.063*
C21	1.2093 (3)	0.5178 (3)	0.5862 (2)	0.0490 (7)
H21	1.2502	0.5992	0.5568	0.059*
C22	1.1058 (3)	0.3970 (3)	0.53216 (19)	0.0399 (6)
H22	1.0781	0.3964	0.4664	0.048*
C23	−0.3161 (3)	0.3805 (3)	0.03986 (17)	0.0383 (5)
C24	0.2211 (3)	−0.1283 (3)	0.08425 (16)	0.0389 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0272 (2)	0.0509 (3)	0.0339 (2)	0.01463 (18)	0.00743 (16)	0.01850 (18)
Cu2	0.0257 (2)	0.0606 (3)	0.0262 (2)	0.00673 (19)	0.00434 (16)	0.01022 (18)
S1	0.0396 (4)	0.0621 (5)	0.0905 (6)	0.0055 (3)	0.0312 (4)	−0.0025 (4)
S2	0.0370 (4)	0.0830 (5)	0.0544 (4)	0.0093 (4)	0.0220 (3)	0.0063 (4)
O1	0.0587 (12)	0.0689 (13)	0.0468 (11)	0.0412 (10)	0.0110 (9)	0.0079 (9)
O2	0.0478 (10)	0.0405 (9)	0.0342 (9)	0.0092 (8)	0.0059 (8)	0.0096 (7)
N1	0.0362 (11)	0.0484 (12)	0.0335 (11)	0.0195 (9)	0.0093 (9)	0.0135 (9)
N2	0.0566 (15)	0.0827 (17)	0.0481 (13)	0.0430 (13)	0.0246 (11)	0.0305 (12)
N3	0.0417 (12)	0.0471 (12)	0.0368 (11)	0.0239 (10)	0.0080 (9)	0.0110 (9)
N4	0.0322 (10)	0.0539 (13)	0.0287 (10)	0.0148 (9)	0.0040 (8)	0.0041 (9)
N5	0.0339 (10)	0.0441 (11)	0.0282 (10)	0.0166 (9)	0.0058 (8)	0.0038 (8)
N6	0.0455 (13)	0.0842 (17)	0.0347 (12)	0.0363 (12)	0.0103 (10)	0.0066 (11)
N7	0.0316 (11)	0.0507 (12)	0.0449 (12)	0.0125 (10)	0.0092 (9)	0.0139 (10)
N8	0.0356 (12)	0.0636 (14)	0.0350 (11)	0.0089 (10)	0.0086 (9)	0.0146 (10)
C1	0.0421 (14)	0.0592 (16)	0.0326 (13)	0.0273 (13)	0.0097 (11)	0.0109 (11)
C2	0.0566 (17)	0.083 (2)	0.0437 (15)	0.0475 (16)	0.0212 (13)	0.0292 (14)
C3	0.0595 (17)	0.0524 (16)	0.0441 (15)	0.0351 (14)	0.0031 (13)	0.0099 (12)
C4	0.0398 (13)	0.0432 (14)	0.0411 (14)	0.0208 (11)	0.0077 (11)	0.0132 (11)
C5	0.0314 (12)	0.0349 (12)	0.0463 (14)	0.0131 (10)	0.0116 (11)	0.0139 (10)
C6	0.0292 (12)	0.0348 (12)	0.0418 (13)	0.0126 (10)	0.0098 (10)	0.0140 (10)
C7	0.0386 (13)	0.0413 (14)	0.0508 (15)	0.0190 (11)	0.0076 (11)	0.0102 (11)
C8	0.0498 (16)	0.0441 (15)	0.0499 (16)	0.0176 (12)	0.0085 (13)	0.0001 (12)
C9	0.0457 (15)	0.0522 (16)	0.0431 (15)	0.0118 (13)	0.0013 (12)	0.0059 (12)
C10	0.0400 (14)	0.0588 (17)	0.0522 (16)	0.0237 (13)	0.0039 (12)	0.0136 (13)
C11	0.0383 (14)	0.0491 (15)	0.0455 (15)	0.0222 (12)	0.0116 (11)	0.0126 (11)
C12	0.0466 (15)	0.0775 (19)	0.0302 (13)	0.0323 (14)	0.0097 (11)	0.0047 (12)
C13	0.0321 (12)	0.0490 (14)	0.0308 (12)	0.0154 (11)	0.0059 (10)	0.0064 (10)
C14	0.0366 (13)	0.0448 (13)	0.0275 (12)	0.0157 (11)	0.0070 (10)	0.0069 (10)
C15	0.0399 (13)	0.0397 (13)	0.0296 (12)	0.0143 (11)	0.0077 (10)	0.0082 (10)
C16	0.0306 (12)	0.0372 (12)	0.0319 (12)	0.0178 (10)	0.0087 (9)	0.0078 (10)
C17	0.0303 (12)	0.0354 (12)	0.0339 (12)	0.0170 (10)	0.0087 (9)	0.0036 (9)
C18	0.0411 (14)	0.0434 (14)	0.0386 (14)	0.0188 (11)	0.0109 (11)	0.0018 (11)
C19	0.0485 (16)	0.0588 (17)	0.0396 (14)	0.0210 (13)	0.0045 (12)	−0.0120 (12)
C20	0.0409 (15)	0.0437 (15)	0.068 (2)	0.0114 (12)	0.0084 (13)	−0.0138 (13)
C21	0.0400 (14)	0.0375 (14)	0.071 (2)	0.0130 (12)	0.0187 (13)	0.0059 (13)
C22	0.0359 (13)	0.0403 (13)	0.0466 (14)	0.0163 (11)	0.0111 (11)	0.0085 (11)
C23	0.0367 (14)	0.0402 (13)	0.0372 (13)	0.0137 (11)	0.0066 (10)	0.0031 (10)
C24	0.0365 (14)	0.0503 (14)	0.0264 (12)	0.0132 (12)	0.0040 (10)	0.0059 (10)

Geometric parameters (Å, º) top

Cu1—N7ⁱ	1.955 (2)	C4—H4B	0.9700
Cu1—N7	1.955 (2)	C5—C6	1.494 (3)
Cu1—N1ⁱ	2.0150 (18)	C6—C7	1.387 (3)
Cu1—N1	2.0150 (18)	C6—C11	1.400 (3)
Cu2—N8ⁱⁱ	1.966 (2)	C7—C8	1.383 (4)
Cu2—N8	1.966 (2)	C7—H7	0.9300
Cu2—N4	1.9771 (19)	C8—C9	1.377 (4)
Cu2—N4ⁱⁱ	1.9771 (19)	C8—H8	0.9300
S1—C23	1.629 (3)	C9—C10	1.379 (4)
S2—C24	1.626 (3)	C9—H9	0.9300
O1—C5	1.213 (3)	C10—C11	1.367 (4)
O2—C16	1.221 (3)	C10—H10	0.9300
N1—C1	1.325 (3)	C11—H11	0.9300
N1—C2	1.348 (3)	C12—H12	0.9300
N2—C2	1.307 (3)	C13—H13	0.9300
N2—N3	1.355 (3)	C14—C15	1.506 (3)
N3—C1	1.315 (3)	C14—H14A	0.9700
N3—C3	1.466 (3)	C14—H14B	0.9700
N4—C13	1.318 (3)	C15—C16	1.501 (3)
N4—C12	1.356 (3)	C15—H15A	0.9700
N5—C13	1.318 (3)	C15—H15B	0.9700
N5—N6	1.359 (3)	C16—C17	1.490 (3)
N5—C14	1.451 (3)	C17—C18	1.390 (3)
N6—C12	1.297 (3)	C17—C22	1.402 (3)
N7—C23	1.149 (3)	C18—C19	1.375 (4)
N8—C24	1.152 (3)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.385 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.511 (4)	C20—C21	1.384 (4)
C3—H3A	0.9700	C20—H20	0.9300
C3—H3B	0.9700	C21—C22	1.380 (4)
C4—C5	1.507 (3)	C21—H21	0.9300
C4—H4A	0.9700	C22—H22	0.9300

N7ⁱ—Cu1—N7	180.00 (18)	C6—C7—H7	119.8
N7ⁱ—Cu1—N1ⁱ	90.26 (8)	C9—C8—C7	120.4 (3)
N7—Cu1—N1ⁱ	89.74 (8)	C9—C8—H8	119.8
N7ⁱ—Cu1—N1	89.74 (8)	C7—C8—H8	119.8
N7—Cu1—N1	90.26 (8)	C8—C9—C10	119.7 (3)
N1ⁱ—Cu1—N1	180.00 (11)	C8—C9—H9	120.1
N8ⁱⁱ—Cu2—N8	180.00 (19)	C10—C9—H9	120.1
N8ⁱⁱ—Cu2—N4	89.33 (8)	C11—C10—C9	120.1 (2)
N8—Cu2—N4	90.67 (8)	C11—C10—H10	119.9
N8ⁱⁱ—Cu2—N4ⁱⁱ	90.67 (8)	C9—C10—H10	119.9
N8—Cu2—N4ⁱⁱ	89.33 (8)	C10—C11—C6	121.2 (2)
N4—Cu2—N4ⁱⁱ	180.00 (16)	C10—C11—H11	119.4
C1—N1—C2	102.3 (2)	C6—C11—H11	119.4
C1—N1—Cu1	129.55 (16)	N6—C12—N4	114.5 (2)
C2—N1—Cu1	128.06 (16)	N6—C12—H12	122.8
C2—N2—N3	102.5 (2)	N4—C12—H12	122.8
C1—N3—N2	109.74 (19)	N4—C13—N5	109.8 (2)
C1—N3—C3	129.3 (2)	N4—C13—H13	125.1
N2—N3—C3	120.9 (2)	N5—C13—H13	125.1
C13—N4—C12	103.1 (2)	N5—C14—C15	110.65 (18)
C13—N4—Cu2	126.30 (16)	N5—C14—H14A	109.5
C12—N4—Cu2	130.52 (16)	C15—C14—H14A	109.5
C13—N5—N6	110.04 (19)	N5—C14—H14B	109.5
C13—N5—C14	128.9 (2)	C15—C14—H14B	109.5
N6—N5—C14	121.02 (19)	H14A—C14—H14B	108.1
C12—N6—N5	102.6 (2)	C16—C15—C14	112.52 (18)
C23—N7—Cu1	169.1 (2)	C16—C15—H15A	109.1
C24—N8—Cu2	163.5 (2)	C14—C15—H15A	109.1
N3—C1—N1	110.6 (2)	C16—C15—H15B	109.1
N3—C1—H1	124.7	C14—C15—H15B	109.1
N1—C1—H1	124.7	H15A—C15—H15B	107.8
N2—C2—N1	114.9 (2)	O2—C16—C17	120.8 (2)
N2—C2—H2	122.6	O2—C16—C15	120.6 (2)
N1—C2—H2	122.6	C17—C16—C15	118.55 (19)
N3—C3—C4	110.8 (2)	C18—C17—C22	119.4 (2)
N3—C3—H3A	109.5	C18—C17—C16	119.2 (2)
C4—C3—H3A	109.5	C22—C17—C16	121.4 (2)
N3—C3—H3B	109.5	C19—C18—C17	120.4 (2)
C4—C3—H3B	109.5	C19—C18—H18	119.8
H3A—C3—H3B	108.1	C17—C18—H18	119.8
C5—C4—C3	113.0 (2)	C18—C19—C20	120.1 (3)
C5—C4—H4A	109.0	C18—C19—H19	120.0
C3—C4—H4A	109.0	C20—C19—H19	120.0
C5—C4—H4B	109.0	C21—C20—C19	120.1 (2)
C3—C4—H4B	109.0	C21—C20—H20	120.0
H4A—C4—H4B	107.8	C19—C20—H20	120.0
O1—C5—C6	120.9 (2)	C22—C21—C20	120.3 (3)
O1—C5—C4	120.6 (2)	C22—C21—H21	119.8
C6—C5—C4	118.5 (2)	C20—C21—H21	119.8
C7—C6—C11	118.1 (2)	C21—C22—C17	119.7 (2)
C7—C6—C5	123.3 (2)	C21—C22—H22	120.2
C11—C6—C5	118.6 (2)	C17—C22—H22	120.2
C8—C7—C6	120.4 (2)	N7—C23—S1	178.5 (2)
C8—C7—H7	119.8	N8—C24—S2	179.5 (3)

N7ⁱ—Cu1—N1—C1	−34.9 (2)	C11—C6—C7—C8	0.3 (4)
N7—Cu1—N1—C1	145.1 (2)	C5—C6—C7—C8	−179.5 (2)
N7ⁱ—Cu1—N1—C2	149.3 (2)	C6—C7—C8—C9	0.8 (4)
N7—Cu1—N1—C2	−30.7 (2)	C7—C8—C9—C10	−0.9 (4)
C2—N2—N3—C1	0.7 (3)	C8—C9—C10—C11	−0.1 (4)
C2—N2—N3—C3	−176.3 (3)	C9—C10—C11—C6	1.2 (4)
N8ⁱⁱ—Cu2—N4—C13	157.5 (2)	C7—C6—C11—C10	−1.3 (4)
N8—Cu2—N4—C13	−22.5 (2)	C5—C6—C11—C10	178.5 (2)
N8ⁱⁱ—Cu2—N4—C12	−27.2 (2)	N5—N6—C12—N4	0.7 (3)
N8—Cu2—N4—C12	152.8 (2)	C13—N4—C12—N6	−0.3 (3)
C13—N5—N6—C12	−0.9 (3)	Cu2—N4—C12—N6	−176.39 (19)
C14—N5—N6—C12	−179.9 (2)	C12—N4—C13—N5	−0.3 (3)
N1ⁱ—Cu1—N7—C23	117.2 (11)	Cu2—N4—C13—N5	176.02 (16)
N1—Cu1—N7—C23	−62.8 (11)	N6—N5—C13—N4	0.8 (3)
N4—Cu2—N8—C24	−146.7 (8)	C14—N5—C13—N4	179.7 (2)
N4ⁱⁱ—Cu2—N8—C24	33.3 (8)	C13—N5—C14—C15	−107.1 (3)
N2—N3—C1—N1	−0.7 (3)	N6—N5—C14—C15	71.7 (3)
C3—N3—C1—N1	176.0 (2)	N5—C14—C15—C16	−172.76 (19)
C2—N1—C1—N3	0.4 (3)	C14—C15—C16—O2	2.3 (3)
Cu1—N1—C1—N3	−176.23 (17)	C14—C15—C16—C17	−177.49 (19)
N3—N2—C2—N1	−0.5 (4)	O2—C16—C17—C18	0.7 (3)
C1—N1—C2—N2	0.1 (3)	C15—C16—C17—C18	−179.5 (2)
Cu1—N1—C2—N2	176.8 (2)	O2—C16—C17—C22	179.9 (2)
C1—N3—C3—C4	143.1 (3)	C15—C16—C17—C22	−0.3 (3)
N2—N3—C3—C4	−40.5 (3)	C22—C17—C18—C19	−0.1 (3)
N3—C3—C4—C5	−166.5 (2)	C16—C17—C18—C19	179.1 (2)
C3—C4—C5—O1	5.0 (3)	C17—C18—C19—C20	0.8 (4)
C3—C4—C5—C6	−176.4 (2)	C18—C19—C20—C21	−0.6 (4)
O1—C5—C6—C7	174.5 (2)	C19—C20—C21—C22	−0.2 (4)
C4—C5—C6—C7	−4.1 (3)	C20—C21—C22—C17	0.9 (4)
O1—C5—C6—C11	−5.3 (3)	C18—C17—C22—C21	−0.8 (3)
C4—C5—C6—C11	176.0 (2)	C16—C17—C22—C21	−179.9 (2)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.58	3.330 (3)	138

Experimental details

Crystal data
Chemical formula	[Cu(NCS)₂(C₁₁H₁₁N₃O)₂]
M_r	582.16
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.8643 (8), 10.1267 (9), 14.3538 (12)
α, β, γ (°)	91.149 (1), 101.270 (1), 110.857 (1)
V (Å³)	1307.75 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.28 × 0.24 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.749, 0.848
No. of measured, independent and observed [I > 2σ(I)] reflections	7171, 4559, 3860
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.091, 1.08
No. of reflections	4559
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.58	3.330 (3)	138

Acknowledgements

The authors acknowledge financial support from the Special Fund for Central Universities (grant No. ZXH2009D011), the Natural Science Foundation of Tianjin (grant No. 09JCYBJC04200), the National Natural Science Foundation of China Civil Aviation Administration of China (grant No. 61079010) and the Scientific Research Foundation of Civil Aviation University of China (grant No. 2011KYS05).

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, J.-H. & Cai, H. (2007). Acta Cryst. E63, m1322–m1324. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yue, Y.-F., Gao, E.-Q., Fang, C.-J., Zheng, T., Liang, J. & Yan, C.-H. (2008). Cryst. Growth Des. 9, 3295–3301. Web of Science CSD CrossRef Google Scholar

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