{N,N-Dimethyl-N′-[phen­yl(2-pyrid­yl)methyl­ene]ethane-1,2-diamine-κ3N,N′,N′′}dithio­cyanato-κN,κS-copper(II)

Zhang, X.-Q.; Li, C.-Y.; Bian, H.-D.; Yu, Q.; Liang, H.

doi:10.1107/S1600536809048594

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1610

doi:10.1107/S1600536809048594

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{N,N-Dimethyl-N′-[phenyl(2-pyridyl)methylene]ethane-1,2-diamine-κ³N,N′,N′′}dithiocyanato-κN,κS-copper(II)

Xiu-Qing Zhang,^a Chun-Ying Li,^a He-Dong Bian,^a Qing Yu ^a and Hong Liang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, Guangxi 541004, People's Republic of China
^*Correspondence e-mail: gxnuchem312@yahoo.com.cn

(Received 4 September 2009; accepted 16 November 2009; online 21 November 2009)

In the title complex, [Cu(NCS)₂(C₁₆H₁₉N₃)], the Cu^II atom is coordinated by a total of four N atoms; three from one tridentate Schiff base ligand and one from one of the NCS⁻ ions. The S atom from the other NCS⁻ ion completes the distorted square-pyramidal coordination.

Related literature

For general background to Schiff base complexes, see: Shi et al. (2004 ); Chandra & Sangeetika (2004 ); Ramesh & Maheswaran (2003 ); Guo et al. (2009 ). For a description of the geometry of five-coordinated metal complexes, see: Addison et al. (1984 ).

Experimental

Crystal data

[Cu(NCS)₂(C₁₆H₁₉N₃)]
M_r = 433.04
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6524 (13) Å
b = 9.2048 (15) Å
c = 27.931 (5) Å
V = 1967.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.33 mm⁻¹
T = 294 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.748, T_max = 1.000
11093 measured reflections
3978 independent reflections
3035 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.130
S = 1.07
3978 reflections
238 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048594/kj2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048594/kj2135Isup2.hkl

checkCIF report

Comment top

Schiff base ligands have been extensively studied in coordination chemistry mainly due to their facile synthesis, easily tunable steric, electronic properties and good solubility in common solvents (Shi et al., 2004). Schiff bases have very wide applications as antibacterial, antiviral, antifungal agents (Chandra et al., 2004; Ramesh et al., 2003), and anticancer drugs (Guo et al., 2009). Herein, we report the Cu^II complex with the related Schiff base ligand N,N-dimethyl-N'-(α-(2-pyridyl)benzylidene)ethane-1,2-diamine. The molecular structure of the title compound is shown in Fig. 1. The coordination polyhedron could be determined by using the index τ = (β - α)/60, where β is the largest angle and α is the second. This index is unity for trigonal-bipyramidal geometry and zero for square-pyramidal geometry (Addison et al., 1984). The calculated value for the title compound 0.08, indicating a slightly distorted square pyramidal geometry for the copper atoms. The basal sites are occupied by four nitrogen atoms from one ligand and one NCS^- ion with the Cu—N bond lengths ranging from 1.937 (4) to 2.071 (4) Å. In the apical position, another NCS^- ion S coordinates to Cu^II atom with the Cu—S bond length of 2.679 (2) Å. All bond distances and bond angles have normal values.The dihedral angle between the benzene and pyridine rings is 69.22 (2)°.

Related literature top

For general background to Schiff base complexes, see: Shi et al. (2004); Chandra & Sangeetika (2004); Ramesh & Maheswaran (2003); Guo et al. (2009). For a description of the geometry of five-coordinated metal complexes, see: Addison et al. (1984).

Experimental top

2-Benzoylpyridine (0.5 mmol) in 5 ml of methanol solution was added to 5 ml of methanol solution containing 0.5 mmol of N,N-dimethylethyldiamine. The solution was stirred for 4 h at 60 °C. Then, 0.5 mmol CuSO₄.5H₂O in 5 ml distilled water and 1 mmol NH₄SCN solid was added. The mixture was stirred at 60 °C for 2 h and then cooled and filtered. The filtrate was allowed to slowly evaporate at room temperature. One month later, blue block crystal was obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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

Fig. 1. A view of the molecular structure of (I) with the atom-numbering scheme and 30% displacement ellipsoids. All H atoms were omitted for clarity.

{N,N-Dimethyl-N'-[phenyl(2-pyridyl)methylene]ethane- 1,2-diamine-κ³N,N',N''}dithiocyanato- κN,κS-copper(II) top

Crystal data top

[Cu(NCS)₂(C₁₆H₁₉N₃)]	D_x = 1.462 Mg m⁻³
M_r = 433.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3480 reflections
a = 7.6524 (13) Å	θ = 2.7–25.6°
b = 9.2048 (15) Å	µ = 1.33 mm⁻¹
c = 27.931 (5) Å	T = 294 K
V = 1967.4 (6) Å³	Block, blue
Z = 4	0.30 × 0.24 × 0.20 mm
F(000) = 892

Data collection top

Bruker APEXII CCD area-detector diffractometer	3978 independent reflections
Radiation source: fine-focus sealed tube	3035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.748, T_max = 1.000	k = −11→9
11093 measured reflections	l = −34→31

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0567P)² + 2.0946P] where P = (F_o² + 2F_c²)/3
3978 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.80 e Å⁻³
6 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(NCS)₂(C₁₆H₁₉N₃)]	V = 1967.4 (6) Å³
M_r = 433.04	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6524 (13) Å	µ = 1.33 mm⁻¹
b = 9.2048 (15) Å	T = 294 K
c = 27.931 (5) Å	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3978 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3035 reflections with I > 2σ(I)
T_min = 0.748, T_max = 1.000	R_int = 0.034
11093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	6 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.07	Δρ_max = 0.80 e Å⁻³
3978 reflections	Δρ_min = −0.51 e Å⁻³
238 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	0.26036 (8)	0.95205 (6)	0.07382 (2)	0.04339 (19)
S1	−0.0307 (2)	0.9109 (2)	−0.07293 (6)	0.0670 (5)
S2	0.0488 (3)	1.1662 (2)	0.10308 (7)	0.0735 (5)
N1	0.1524 (7)	0.9185 (6)	0.01206 (16)	0.0609 (14)
N2	−0.0282 (8)	1.0836 (9)	0.1945 (2)	0.098 (2)
N3	0.1284 (5)	0.7992 (5)	0.11202 (15)	0.0415 (10)
N4	0.4058 (5)	0.9435 (5)	0.13148 (14)	0.0391 (9)
N5	0.4643 (6)	1.0786 (5)	0.04853 (14)	0.0429 (10)
C1	0.0763 (7)	0.9159 (6)	−0.02339 (18)	0.0422 (12)
C2	0.0070 (9)	1.1144 (8)	0.1584 (3)	0.071 (2)
C3	−0.0085 (7)	0.7208 (7)	0.0973 (2)	0.0509 (14)
H3	−0.0606	0.7416	0.0680	0.061*
C4	−0.0730 (9)	0.6097 (9)	0.1250 (3)	0.078 (2)
H4	−0.1645	0.5527	0.1137	0.093*
C5	−0.0016 (9)	0.5823 (8)	0.1698 (3)	0.077 (2)
H5	−0.0454	0.5080	0.1889	0.092*
C6	0.1341 (8)	0.6666 (7)	0.1854 (2)	0.0561 (16)
H6	0.1821	0.6520	0.2156	0.067*
C7	0.1993 (6)	0.7740 (6)	0.15551 (17)	0.0388 (12)
C8	0.3525 (7)	0.8643 (6)	0.16633 (16)	0.0376 (11)
C9	0.4422 (7)	0.8568 (6)	0.21348 (18)	0.0414 (12)
C10	0.6136 (9)	0.8125 (9)	0.2169 (3)	0.075 (2)
H10	0.6737	0.7854	0.1894	0.090*
C11	0.6961 (10)	0.8079 (9)	0.2600 (3)	0.083 (2)
H11	0.8103	0.7739	0.2618	0.100*
C12	0.6143 (10)	0.8520 (9)	0.2999 (2)	0.072 (2)
H12	0.6727	0.8523	0.3291	0.086*
C13	0.4464 (12)	0.8959 (10)	0.2973 (2)	0.094 (3)
H13	0.3889	0.9248	0.3250	0.113*
C14	0.3591 (10)	0.8986 (9)	0.2545 (2)	0.076 (2)
H14	0.2433	0.9289	0.2534	0.091*
C15	0.5594 (7)	1.0370 (7)	0.13190 (19)	0.0511 (14)
H15A	0.6642	0.9799	0.1265	0.061*
H15B	0.5699	1.0855	0.1626	0.061*
C16	0.5371 (8)	1.1467 (6)	0.0926 (2)	0.0508 (14)
H16A	0.4591	1.2232	0.1034	0.061*
H16B	0.6493	1.1904	0.0853	0.061*
C17	0.4088 (9)	1.1937 (7)	0.0152 (2)	0.0620 (17)
H17A	0.5065	1.2552	0.0080	0.093*
H17B	0.3179	1.2505	0.0298	0.093*
H17C	0.3656	1.1505	−0.0137	0.093*
C18	0.5928 (9)	0.9836 (8)	0.0258 (2)	0.0673 (18)
H18A	0.5454	0.9456	−0.0034	0.101*
H18B	0.6207	0.9049	0.0470	0.101*
H18C	0.6969	1.0380	0.0189	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0457 (3)	0.0544 (3)	0.0300 (3)	−0.0063 (4)	−0.0057 (3)	0.0011 (3)
S1	0.0712 (10)	0.0874 (12)	0.0424 (8)	−0.0034 (9)	−0.0207 (8)	−0.0084 (9)
S2	0.0689 (11)	0.0779 (12)	0.0737 (12)	0.0142 (10)	−0.0035 (9)	0.0054 (10)
N1	0.071 (3)	0.078 (4)	0.034 (2)	−0.011 (3)	−0.014 (2)	0.000 (3)
N2	0.075 (4)	0.151 (6)	0.067 (4)	−0.047 (4)	0.029 (3)	−0.049 (4)
N3	0.035 (2)	0.050 (3)	0.040 (2)	−0.003 (2)	0.0030 (19)	−0.007 (2)
N4	0.038 (2)	0.047 (2)	0.032 (2)	−0.002 (2)	−0.0039 (17)	0.000 (2)
N5	0.047 (2)	0.047 (3)	0.035 (2)	−0.005 (2)	0.0029 (19)	0.006 (2)
C1	0.046 (3)	0.043 (3)	0.038 (3)	−0.009 (2)	0.000 (2)	−0.005 (2)
C2	0.054 (4)	0.080 (5)	0.079 (5)	−0.010 (3)	−0.009 (4)	−0.020 (4)
C3	0.041 (3)	0.064 (4)	0.048 (3)	−0.003 (3)	0.004 (3)	−0.002 (3)
C4	0.050 (4)	0.088 (5)	0.095 (6)	−0.030 (4)	−0.005 (4)	0.009 (4)
C5	0.054 (4)	0.083 (5)	0.094 (5)	−0.025 (4)	0.011 (4)	0.027 (4)
C6	0.048 (3)	0.070 (4)	0.050 (3)	0.000 (3)	−0.001 (3)	0.018 (3)
C7	0.032 (3)	0.052 (3)	0.032 (3)	0.004 (2)	0.006 (2)	−0.001 (2)
C8	0.041 (3)	0.042 (3)	0.030 (2)	0.015 (2)	0.002 (2)	−0.003 (2)
C9	0.048 (3)	0.043 (3)	0.033 (3)	0.004 (3)	−0.004 (2)	0.001 (2)
C10	0.058 (4)	0.111 (6)	0.056 (4)	0.034 (4)	−0.006 (3)	0.008 (4)
C11	0.064 (5)	0.124 (7)	0.061 (4)	0.016 (4)	−0.023 (3)	0.016 (4)
C12	0.081 (5)	0.085 (5)	0.050 (4)	−0.014 (4)	−0.026 (4)	0.022 (4)
C13	0.107 (7)	0.134 (8)	0.041 (4)	0.031 (6)	−0.009 (4)	−0.007 (4)
C14	0.069 (4)	0.124 (6)	0.035 (3)	0.044 (4)	−0.006 (3)	−0.010 (4)
C15	0.045 (3)	0.063 (4)	0.045 (3)	−0.004 (3)	−0.011 (2)	0.006 (3)
C16	0.059 (3)	0.051 (3)	0.043 (3)	−0.010 (3)	−0.009 (3)	0.003 (3)
C17	0.071 (4)	0.069 (4)	0.046 (3)	−0.010 (3)	−0.002 (3)	0.019 (3)
C18	0.068 (4)	0.067 (4)	0.067 (4)	0.002 (3)	0.019 (3)	0.002 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.937 (4)	C7—C8	1.468 (7)
Cu1—N4	1.959 (4)	C8—C9	1.487 (7)
Cu1—N3	2.034 (4)	C9—C14	1.365 (8)
Cu1—N5	2.071 (4)	C9—C10	1.376 (8)
Cu1—S2	2.679 (2)	C10—C11	1.361 (9)
S1—C1	1.609 (5)	C10—H10	0.9300
S2—C2	1.648 (9)	C11—C12	1.341 (10)
N1—C1	1.149 (7)	C11—H11	0.9300
N2—C2	1.082 (9)	C12—C13	1.349 (11)
N3—C3	1.337 (7)	C12—H12	0.9300
N3—C7	1.351 (6)	C13—C14	1.369 (9)
N4—C8	1.283 (6)	C13—H13	0.9300
N4—C15	1.457 (7)	C14—H14	0.9300
N5—C18	1.461 (7)	C15—C16	1.501 (8)
N5—C17	1.472 (7)	C15—H15A	0.9700
N5—C16	1.490 (7)	C15—H15B	0.9700
C3—C4	1.373 (9)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.389 (10)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.368 (9)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.386 (8)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600

N1—Cu1—N4	165.4 (2)	C7—C8—C9	121.7 (4)
N1—Cu1—N3	98.3 (2)	C14—C9—C10	118.0 (6)
N4—Cu1—N3	79.81 (18)	C14—C9—C8	121.0 (5)
N1—Cu1—N5	96.2 (2)	C10—C9—C8	121.0 (5)
N4—Cu1—N5	82.82 (17)	C11—C10—C9	120.8 (7)
N3—Cu1—N5	160.36 (17)	C11—C10—H10	119.6
N1—Cu1—S2	97.53 (18)	C9—C10—H10	119.6
N4—Cu1—S2	97.02 (13)	C12—C11—C10	120.7 (7)
N3—Cu1—S2	92.79 (13)	C12—C11—H11	119.7
N5—Cu1—S2	98.38 (13)	C10—C11—H11	119.7
C2—S2—Cu1	101.0 (3)	C11—C12—C13	119.3 (6)
C1—N1—Cu1	170.7 (5)	C11—C12—H12	120.4
C3—N3—C7	119.9 (5)	C13—C12—H12	120.4
C3—N3—Cu1	127.0 (4)	C12—C13—C14	121.2 (7)
C7—N3—Cu1	113.0 (3)	C12—C13—H13	119.4
C8—N4—C15	125.9 (4)	C14—C13—H13	119.4
C8—N4—Cu1	117.8 (3)	C9—C14—C13	120.0 (7)
C15—N4—Cu1	116.2 (3)	C9—C14—H14	120.0
C18—N5—C17	110.5 (5)	C13—C14—H14	120.0
C18—N5—C16	111.0 (5)	N4—C15—C16	107.4 (4)
C17—N5—C16	109.1 (4)	N4—C15—H15A	110.2
C18—N5—Cu1	108.6 (4)	C16—C15—H15A	110.2
C17—N5—Cu1	113.7 (4)	N4—C15—H15B	110.2
C16—N5—Cu1	103.7 (3)	C16—C15—H15B	110.2
N1—C1—S1	179.5 (6)	H15A—C15—H15B	108.5
N2—C2—S2	176.5 (8)	N5—C16—C15	111.3 (5)
N3—C3—C4	120.7 (6)	N5—C16—H16A	109.4
N3—C3—H3	119.6	C15—C16—H16A	109.4
C4—C3—H3	119.6	N5—C16—H16B	109.4
C3—C4—C5	120.0 (6)	C15—C16—H16B	109.4
C3—C4—H4	120.0	H16A—C16—H16B	108.0
C5—C4—H4	120.0	N5—C17—H17A	109.5
C6—C5—C4	118.9 (6)	N5—C17—H17B	109.5
C6—C5—H5	120.6	H17A—C17—H17B	109.5
C4—C5—H5	120.6	N5—C17—H17C	109.5
C5—C6—C7	119.1 (6)	H17A—C17—H17C	109.5
C5—C6—H6	120.5	H17B—C17—H17C	109.5
C7—C6—H6	120.5	N5—C18—H18A	109.5
N3—C7—C6	121.3 (5)	N5—C18—H18B	109.5
N3—C7—C8	114.1 (4)	H18A—C18—H18B	109.5
C6—C7—C8	124.5 (5)	N5—C18—H18C	109.5
N4—C8—C7	114.8 (4)	H18A—C18—H18C	109.5
N4—C8—C9	123.5 (5)	H18B—C18—H18C	109.5

N1—Cu1—S2—C2	134.4 (3)	C3—C4—C5—C6	−0.7 (11)
N4—Cu1—S2—C2	−44.5 (3)	C4—C5—C6—C7	−1.7 (10)
N3—Cu1—S2—C2	35.6 (3)	C3—N3—C7—C6	0.7 (8)
N5—Cu1—S2—C2	−128.2 (3)	Cu1—N3—C7—C6	−175.7 (4)
N1—Cu1—N3—C3	−8.9 (5)	C3—N3—C7—C8	177.9 (4)
N4—Cu1—N3—C3	−174.2 (5)	Cu1—N3—C7—C8	1.5 (5)
N5—Cu1—N3—C3	−146.0 (5)	C5—C6—C7—N3	1.7 (9)
S2—Cu1—N3—C3	89.2 (4)	C5—C6—C7—C8	−175.2 (5)
N1—Cu1—N3—C7	167.2 (4)	C15—N4—C8—C7	−176.7 (5)
N4—Cu1—N3—C7	1.9 (3)	Cu1—N4—C8—C7	8.0 (6)
N5—Cu1—N3—C7	30.1 (7)	C15—N4—C8—C9	0.2 (8)
S2—Cu1—N3—C7	−94.7 (3)	Cu1—N4—C8—C9	−175.1 (4)
N1—Cu1—N4—C8	−89.6 (9)	N3—C7—C8—N4	−6.1 (6)
N3—Cu1—N4—C8	−5.7 (4)	C6—C7—C8—N4	171.0 (5)
N5—Cu1—N4—C8	−176.5 (4)	N3—C7—C8—C9	176.9 (4)
S2—Cu1—N4—C8	85.9 (4)	C6—C7—C8—C9	−6.0 (8)
N1—Cu1—N4—C15	94.7 (9)	N4—C8—C9—C14	118.4 (7)
N3—Cu1—N4—C15	178.6 (4)	C7—C8—C9—C14	−64.9 (7)
N5—Cu1—N4—C15	7.8 (4)	N4—C8—C9—C10	−59.2 (8)
S2—Cu1—N4—C15	−89.8 (4)	C7—C8—C9—C10	117.5 (7)
N1—Cu1—N5—C18	−75.9 (4)	C14—C9—C10—C11	1.3 (11)
N4—Cu1—N5—C18	89.4 (4)	C8—C9—C10—C11	179.0 (7)
N3—Cu1—N5—C18	61.5 (7)	C9—C10—C11—C12	−2.7 (13)
S2—Cu1—N5—C18	−174.5 (4)	C10—C11—C12—C13	2.5 (13)
N1—Cu1—N5—C17	47.6 (4)	C11—C12—C13—C14	−1.1 (14)
N4—Cu1—N5—C17	−147.1 (4)	C10—C9—C14—C13	0.1 (11)
N3—Cu1—N5—C17	−175.0 (5)	C8—C9—C14—C13	−177.6 (7)
S2—Cu1—N5—C17	−51.0 (4)	C12—C13—C14—C9	−0.2 (14)
N1—Cu1—N5—C16	165.9 (4)	C8—N4—C15—C16	−159.8 (5)
N4—Cu1—N5—C16	−28.7 (3)	Cu1—N4—C15—C16	15.6 (6)
N3—Cu1—N5—C16	−56.7 (6)	C18—N5—C16—C15	−70.3 (6)
S2—Cu1—N5—C16	67.3 (3)	C17—N5—C16—C15	167.6 (5)
C7—N3—C3—C4	−3.2 (8)	Cu1—N5—C16—C15	46.1 (5)
Cu1—N3—C3—C4	172.7 (5)	N4—C15—C16—N5	−41.5 (6)
N3—C3—C4—C5	3.2 (10)

Experimental details

Crystal data
Chemical formula	[Cu(NCS)₂(C₁₆H₁₉N₃)]
M_r	433.04
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	7.6524 (13), 9.2048 (15), 27.931 (5)
V (Å³)	1967.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.748, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11093, 3978, 3035
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.130, 1.07
No. of reflections	3978
No. of parameters	238
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.51

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge the Science Foundation of Guangxi (No.07311052) and the Teaching and Research Award Programme for Outstanding Young Teachers in Higher Education Institutions of MOE, China.

References

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