(1-{(E)-[Phen­yl(pyridin-2-yl-κN)methyl­idene]amino-κN}pyrrolidin-2-one-κO)bis­(thio­cyanato-κN)copper(II)

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

doi:10.1107/S1600536812039918

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1302

https://doi.org/10.1107/S1600536812039918

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(1-{(E)-[Phenyl(pyridin-2-yl-κN)methylidene]amino-κN}pyrrolidin-2-one-κO)bis(thiocyanato-κN)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 18 September 2012; accepted 20 September 2012; online 26 September 2012)

The Cu^II atom in the title compound, [Cu(NCS)₂(C₁₆H₁₅N₃O)], is bonded to the N atoms of two thiocyanate ions, and is N,N′-chelated by the Schiff base ligand. The four N atoms surround the metal atom to form a distorted square; the square environment is distorted towards a square pyramid by a long Cu⋯O interaction. In the crystal, two C atoms of the pyrrolidin-2-one ring are disordered over two positions in a 1:1 ratio.

Related literature

For the copper dichloride adduct of the Schiff base, see: Kunnath et al. (2012 ).

Experimental

Crystal data

[Cu(NCS)₂(C₁₆H₁₅N₃O)]
M_r = 445.01
Monoclinic, C 2/c
a = 11.8883 (3) Å
b = 13.3578 (3) Å
c = 23.9669 (6) Å
β = 98.596 (1)°
V = 3763.23 (16) Å³
Z = 8
Mo Kα radiation
μ = 1.40 mm⁻¹
T = 293 K
0.4 × 0.3 × 0.2 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.614, T_max = 1.000
7808 measured reflections
4232 independent reflections
3354 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.169
S = 1.16
4232 reflections
250 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	2.676 (4)
Cu1—N1	1.998 (4)
Cu1—N2	2.000 (3)
Cu1—N4	1.957 (4)
Cu1—N5	1.912 (4)

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: https://doi.org/10.1107/S1600536812039918/xu5623sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039918/xu5623Isup2.hkl

checkCIF report

Comment top

1-[(E)-[Phenyl(pyridin-2-yl)methylidene]amino]pyrrolidine-2-one is a tridentate Schiff base that can only be synthesized in situ; it was isolated as its copper dichloride adduct in an earlier study (Kunnath et al., 2012). In the present copper dithiocyanate adduct (Scheme I, Fig. 1), the geometry is also a square pyramid but the apical O atom lies at 2.676 (4) Å whereas the geometry of the copper dichloride analog is an almost undistorted square pyramid.

Related literature top

For the copper dichloride adduct of the Schiff base, see: Kunnath et al. (2012).

Experimental top

1-[(E)-[Phenyl(pyridin-2-yl)methylidene]amino]pyrrolidine-2-one was synthesized in situ from 2-benzoylpyridine (0.183 g, 1 mmol) and 1-aminopyrrolidin-2-one (0.100 g, 1 mmol) by heating the reactants in methanol for 2 hous. Copper(II) chloride dihydrate (0.170 g, 1 mmol) was added, and the mixture heated for 2 h. Sodium thiocyanate (0.194 g, 2 mmol) was added and the reaction was heated for another for 1 h. The resulting pale green solid was collected and recrystallized from alcohol.

Structure description top

For the copper dichloride adduct of the Schiff base, see: Kunnath et al. (2012).

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(NCS)₂(C₁₆H₁₅N₃O) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the pyrrolidine ring is not shown.

(1-{(E)-[Phenyl(pyridin-2-yl-κN)methylidene]amino- κN}pyrrolidin-2-one-κO)bis(thiocyanato-κN)copper(II) top

Crystal data top

[Cu(NCS)₂(C₁₆H₁₅N₃O)]	F(000) = 1816
M_r = 445.01	D_x = 1.571 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3798 reflections
a = 11.8883 (3) Å	θ = 2.3–28.2°
b = 13.3578 (3) Å	µ = 1.40 mm⁻¹
c = 23.9669 (6) Å	T = 293 K
β = 98.596 (1)°	Prism, green
V = 3763.23 (16) Å³	0.4 × 0.3 × 0.2 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→15
T_min = 0.614, T_max = 1.000	k = −17→15
7808 measured reflections	l = −28→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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0468P)² + 21.4376P] where P = (F_o² + 2F_c²)/3
4232 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.73 e Å⁻³
3 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Cu(NCS)₂(C₁₆H₁₅N₃O)]	V = 3763.23 (16) Å³
M_r = 445.01	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.8883 (3) Å	µ = 1.40 mm⁻¹
b = 13.3578 (3) Å	T = 293 K
c = 23.9669 (6) Å	0.4 × 0.3 × 0.2 mm
β = 98.596 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	4232 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3354 reflections with I > 2σ(I)
T_min = 0.614, T_max = 1.000	R_int = 0.033
7808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	3 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0468P)² + 21.4376P] where P = (F_o² + 2F_c²)/3
4232 reflections	Δρ_max = 0.73 e Å⁻³
250 parameters	Δρ_min = −0.63 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.38438 (5)	0.63120 (5)	0.47230 (2)	0.03878 (19)
S1	0.08245 (15)	0.56173 (18)	0.32832 (8)	0.0762 (6)
S2	0.20280 (18)	0.64256 (14)	0.63148 (7)	0.0733 (5)
N1	0.4851 (3)	0.7508 (3)	0.48791 (15)	0.0313 (8)
N2	0.4894 (3)	0.6106 (3)	0.41547 (14)	0.0301 (8)
N3	0.4722 (3)	0.5290 (3)	0.38127 (15)	0.0324 (8)
N4	0.2510 (3)	0.5904 (4)	0.41915 (19)	0.0467 (10)
N5	0.3145 (4)	0.6345 (4)	0.53914 (19)	0.0524 (11)
O1	0.4251 (3)	0.4376 (3)	0.45491 (14)	0.0466 (9)
C1	0.4875 (4)	0.8152 (4)	0.5301 (2)	0.0389 (10)
H1	0.4366	0.8067	0.5556	0.047*
C2	0.5623 (5)	0.8943 (4)	0.5375 (2)	0.0458 (12)
H2	0.5616	0.9381	0.5676	0.055*
C3	0.6381 (5)	0.9080 (4)	0.5002 (2)	0.0497 (13)
H3	0.6890	0.9613	0.5043	0.060*
C4	0.6367 (4)	0.8401 (4)	0.4559 (2)	0.0423 (11)
H4	0.6878	0.8467	0.4303	0.051*
C5	0.5592 (4)	0.7635 (3)	0.45059 (17)	0.0311 (9)
C6	0.5531 (3)	0.6846 (3)	0.40697 (17)	0.0293 (9)
C7	0.6212 (4)	0.6942 (3)	0.35987 (18)	0.0315 (9)
C8	0.6005 (4)	0.7732 (4)	0.3226 (2)	0.0407 (11)
H8	0.5484	0.8226	0.3285	0.049*
C9	0.6573 (5)	0.7787 (5)	0.2767 (2)	0.0518 (14)
H9	0.6419	0.8309	0.2510	0.062*
C10	0.7366 (5)	0.7074 (5)	0.2687 (2)	0.0563 (16)
H10	0.7751	0.7118	0.2377	0.068*
C11	0.7595 (5)	0.6294 (5)	0.3064 (2)	0.0563 (15)
H11	0.8142	0.5820	0.3011	0.068*
C12	0.7012 (4)	0.6214 (4)	0.3520 (2)	0.0424 (11)
H12	0.7153	0.5682	0.3771	0.051*
C14	0.4536 (5)	0.5269 (5)	0.3197 (2)	0.0565 (16)
H14A	0.5225	0.5440	0.3047	0.068*	0.50
H14B	0.3934	0.5726	0.3044	0.068*	0.50
H14C	0.5252	0.5209	0.3051	0.068*	0.50
H14D	0.4150	0.5870	0.3044	0.068*	0.50
C15	0.420 (2)	0.4208 (13)	0.3069 (19)	0.064 (7)	0.50
H15A	0.4813	0.3862	0.2921	0.077*	0.50
H15B	0.3530	0.4187	0.2784	0.077*	0.50
C16	0.396 (5)	0.370 (3)	0.3602 (13)	0.051 (5)	0.50
H16A	0.3157	0.3546	0.3581	0.062*	0.50
H16B	0.4393	0.3082	0.3670	0.062*	0.50
C15'	0.381 (2)	0.4368 (14)	0.3052 (19)	0.064 (7)	0.50
H15C	0.4003	0.4035	0.2719	0.077*	0.50
H15D	0.3011	0.4539	0.2991	0.077*	0.50
C16'	0.411 (5)	0.372 (3)	0.3574 (13)	0.051 (5)	0.50
H16C	0.3491	0.3279	0.3623	0.062*	0.50
H16D	0.4787	0.3326	0.3549	0.062*	0.50
C17	0.4330 (4)	0.4452 (3)	0.40513 (19)	0.0343 (10)
C18	0.1816 (4)	0.5783 (4)	0.3809 (2)	0.0427 (12)
C19	0.2681 (4)	0.6390 (4)	0.5774 (2)	0.0394 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0356 (3)	0.0437 (3)	0.0407 (3)	−0.0122 (3)	0.0179 (2)	−0.0071 (3)
S1	0.0496 (9)	0.1086 (16)	0.0666 (11)	−0.0120 (9)	−0.0039 (8)	0.0002 (10)
S2	0.0979 (13)	0.0745 (12)	0.0592 (9)	0.0200 (10)	0.0498 (9)	0.0077 (8)
N1	0.0292 (18)	0.0318 (19)	0.0349 (19)	−0.0018 (15)	0.0118 (15)	−0.0001 (15)
N2	0.0351 (19)	0.0295 (19)	0.0273 (17)	−0.0065 (15)	0.0098 (14)	−0.0033 (14)
N3	0.0328 (19)	0.034 (2)	0.0315 (18)	−0.0083 (16)	0.0083 (15)	−0.0046 (15)
N4	0.032 (2)	0.055 (3)	0.054 (3)	−0.0064 (19)	0.008 (2)	−0.006 (2)
N5	0.044 (2)	0.064 (3)	0.054 (3)	−0.015 (2)	0.024 (2)	−0.008 (2)
O1	0.065 (2)	0.0375 (19)	0.0373 (18)	−0.0111 (17)	0.0072 (16)	0.0039 (14)
C1	0.040 (2)	0.038 (3)	0.042 (3)	0.003 (2)	0.014 (2)	−0.003 (2)
C2	0.057 (3)	0.036 (3)	0.046 (3)	−0.002 (2)	0.012 (2)	−0.012 (2)
C3	0.060 (3)	0.042 (3)	0.050 (3)	−0.024 (3)	0.015 (2)	−0.007 (2)
C4	0.046 (3)	0.036 (3)	0.048 (3)	−0.018 (2)	0.018 (2)	−0.005 (2)
C5	0.032 (2)	0.031 (2)	0.032 (2)	−0.0017 (17)	0.0088 (17)	−0.0001 (17)
C6	0.028 (2)	0.028 (2)	0.032 (2)	−0.0042 (17)	0.0074 (17)	−0.0001 (17)
C7	0.032 (2)	0.031 (2)	0.033 (2)	−0.0118 (18)	0.0076 (17)	−0.0056 (17)
C8	0.040 (3)	0.044 (3)	0.040 (2)	−0.010 (2)	0.011 (2)	0.003 (2)
C9	0.050 (3)	0.068 (4)	0.037 (3)	−0.026 (3)	0.006 (2)	0.002 (2)
C10	0.050 (3)	0.082 (4)	0.042 (3)	−0.031 (3)	0.023 (2)	−0.018 (3)
C11	0.044 (3)	0.069 (4)	0.060 (3)	−0.008 (3)	0.021 (3)	−0.026 (3)
C12	0.037 (2)	0.042 (3)	0.051 (3)	−0.005 (2)	0.012 (2)	−0.006 (2)
C14	0.069 (4)	0.069 (4)	0.031 (3)	−0.030 (3)	0.006 (2)	−0.004 (2)
C15	0.079 (17)	0.073 (7)	0.043 (4)	−0.040 (10)	0.021 (14)	−0.021 (7)
C16	0.060 (12)	0.041 (3)	0.053 (4)	−0.020 (5)	0.009 (5)	−0.012 (3)
C15'	0.079 (17)	0.073 (7)	0.043 (4)	−0.040 (10)	0.021 (14)	−0.021 (7)
C16'	0.060 (12)	0.041 (3)	0.053 (4)	−0.020 (5)	0.009 (5)	−0.012 (3)
C17	0.030 (2)	0.031 (2)	0.042 (2)	−0.0041 (18)	0.0071 (18)	−0.0042 (19)
C18	0.035 (3)	0.042 (3)	0.056 (3)	0.000 (2)	0.023 (2)	0.002 (2)
C19	0.039 (2)	0.036 (2)	0.045 (3)	−0.002 (2)	0.012 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Cu1—O1	2.676 (4)	C8—C9	1.376 (7)
Cu1—N1	1.998 (4)	C8—H8	0.9300
Cu1—N2	2.000 (3)	C9—C10	1.373 (9)
Cu1—N4	1.957 (4)	C9—H9	0.9300
Cu1—N5	1.912 (4)	C10—C11	1.380 (9)
S1—C18	1.606 (6)	C10—H10	0.9300
S2—C19	1.608 (5)	C11—C12	1.383 (7)
N1—C1	1.324 (6)	C11—H11	0.9300
N1—C5	1.357 (5)	C12—H12	0.9300
N2—C6	1.280 (5)	C14—C15	1.490 (11)
N2—N3	1.361 (5)	C14—C15'	1.490 (11)
N3—C17	1.370 (6)	C14—H14A	0.9700
N3—C14	1.460 (6)	C14—H14B	0.9700
N4—C18	1.150 (7)	C14—H14C	0.9700
N5—C19	1.141 (6)	C14—H14D	0.9700
O1—C17	1.215 (5)	C15—C16	1.516 (18)
C1—C2	1.376 (7)	C15—H15A	0.9700
C1—H1	0.9300	C15—H15B	0.9700
C2—C3	1.374 (7)	C16—C17	1.492 (9)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.395 (7)	C16—H16B	0.9700
C3—H3	0.9300	C15'—C16'	1.516 (18)
C4—C5	1.369 (6)	C15'—H15C	0.9700
C4—H4	0.9300	C15'—H15D	0.9700
C5—C6	1.478 (6)	C16'—C17	1.493 (9)
C6—C7	1.489 (6)	C16'—H16C	0.9700
C7—C12	1.393 (7)	C16'—H16D	0.9700
C7—C8	1.381 (7)

N5—Cu1—N4	98.09 (19)	C11—C10—H10	119.8
N5—Cu1—N1	98.49 (17)	C12—C11—C10	120.2 (6)
N4—Cu1—N1	138.54 (18)	C12—C11—H11	119.9
N5—Cu1—N2	165.37 (19)	C10—C11—H11	119.9
N4—Cu1—N2	92.65 (16)	C7—C12—C11	119.1 (5)
N1—Cu1—N2	79.61 (14)	C7—C12—H12	120.5
N5—Cu1—O1	105.33 (17)	C11—C12—H12	120.5
N4—Cu1—O1	77.12 (16)	N3—C14—C15	102.9 (18)
N1—Cu1—O1	133.21 (13)	N3—C14—C15'	104.2 (18)
N2—Cu1—O1	67.36 (13)	N3—C14—H14A	111.2
C1—N1—C5	118.6 (4)	C15—C14—H14A	111.2
C1—N1—Cu1	127.3 (3)	N3—C14—H14B	111.2
C5—N1—Cu1	114.0 (3)	C15—C14—H14B	111.2
C6—N2—N3	124.2 (3)	H14A—C14—H14B	109.1
C6—N2—Cu1	116.5 (3)	N3—C14—H14C	110.9
N3—N2—Cu1	117.9 (3)	C15'—C14—H14C	110.9
N2—N3—C17	115.7 (3)	N3—C14—H14D	110.9
N2—N3—C14	127.7 (4)	C15'—C14—H14D	110.9
C17—N3—C14	113.4 (4)	H14C—C14—H14D	108.9
C18—N4—Cu1	166.7 (4)	C14—C15—C16	109 (3)
C19—N5—Cu1	176.4 (5)	C14—C15—H15A	109.8
C17—O1—Cu1	96.6 (3)	C16—C15—H15A	109.8
N1—C1—C2	122.6 (4)	C14—C15—H15B	109.8
N1—C1—H1	118.7	C16—C15—H15B	109.8
C2—C1—H1	118.7	H15A—C15—H15B	108.2
C3—C2—C1	119.5 (5)	C17—C16—C15	103 (3)
C3—C2—H2	120.3	C17—C16—H16A	111.1
C1—C2—H2	120.3	C15—C16—H16A	111.1
C2—C3—C4	118.3 (5)	C17—C16—H16B	111.1
C2—C3—H3	120.8	C15—C16—H16B	111.1
C4—C3—H3	120.8	H16A—C16—H16B	109.1
C5—C4—C3	119.2 (4)	C14—C15'—C16'	102 (3)
C5—C4—H4	120.4	C14—C15'—H15C	111.4
C3—C4—H4	120.4	C16'—C15'—H15C	111.4
N1—C5—C4	121.8 (4)	C14—C15'—H15D	111.4
N1—C5—C6	114.1 (4)	C16'—C15'—H15D	111.4
C4—C5—C6	124.0 (4)	H15C—C15'—H15D	109.2
N2—C6—C5	113.9 (4)	C17—C16'—C15'	105 (3)
N2—C6—C7	126.0 (4)	C17—C16'—H16C	110.8
C5—C6—C7	120.0 (4)	C15'—C16'—H16C	110.8
C12—C7—C8	120.3 (4)	C17—C16'—H16D	110.8
C12—C7—C6	120.1 (4)	C15'—C16'—H16D	110.8
C8—C7—C6	119.5 (4)	H16C—C16'—H16D	108.9
C9—C8—C7	119.8 (5)	O1—C17—N3	124.0 (4)
C9—C8—H8	120.1	O1—C17—C16	126.4 (19)
C7—C8—H8	120.1	N3—C17—C16	109.5 (18)
C10—C9—C8	120.3 (5)	O1—C17—C16'	131.9 (18)
C10—C9—H9	119.9	N3—C17—C16'	104.1 (18)
C8—C9—H9	119.9	N4—C18—S1	178.7 (5)
C9—C10—C11	120.3 (5)	N5—C19—S2	178.7 (5)
C9—C10—H10	119.8

N5—Cu1—N1—C1	−6.5 (4)	N3—N2—C6—C7	−1.5 (7)
N4—Cu1—N1—C1	106.1 (4)	Cu1—N2—C6—C7	−167.7 (3)
N2—Cu1—N1—C1	−171.8 (4)	N1—C5—C6—N2	−8.3 (6)
O1—Cu1—N1—C1	−127.0 (4)	C4—C5—C6—N2	167.9 (5)
N5—Cu1—N1—C5	172.4 (3)	N1—C5—C6—C7	173.9 (4)
N4—Cu1—N1—C5	−75.0 (4)	C4—C5—C6—C7	−9.9 (7)
N2—Cu1—N1—C5	7.1 (3)	N2—C6—C7—C12	−57.0 (6)
O1—Cu1—N1—C5	51.9 (4)	C5—C6—C7—C12	120.5 (5)
N5—Cu1—N2—C6	−96.2 (8)	N2—C6—C7—C8	120.0 (5)
N4—Cu1—N2—C6	126.5 (3)	C5—C6—C7—C8	−62.5 (6)
N1—Cu1—N2—C6	−12.4 (3)	C12—C7—C8—C9	1.6 (7)
O1—Cu1—N2—C6	−158.6 (4)	C6—C7—C8—C9	−175.4 (4)
N5—Cu1—N2—N3	96.7 (7)	C7—C8—C9—C10	−1.8 (7)
N4—Cu1—N2—N3	−40.6 (3)	C8—C9—C10—C11	0.5 (8)
N1—Cu1—N2—N3	−179.5 (3)	C9—C10—C11—C12	1.1 (8)
O1—Cu1—N2—N3	34.3 (3)	C8—C7—C12—C11	−0.1 (7)
C6—N2—N3—C17	159.9 (4)	C6—C7—C12—C11	176.9 (4)
Cu1—N2—N3—C17	−34.1 (5)	C10—C11—C12—C7	−1.3 (8)
C6—N2—N3—C14	−42.1 (7)	N2—N3—C14—C15	−170.4 (12)
Cu1—N2—N3—C14	123.9 (5)	C17—N3—C14—C15	−12.0 (13)
N5—Cu1—N4—C18	144.6 (19)	N2—N3—C14—C15'	−150.3 (13)
N5—Cu1—O1—C17	159.6 (3)	C17—N3—C14—C15'	8.1 (13)
N4—Cu1—O1—C17	64.6 (3)	N3—C14—C15—C16	12 (3)
N1—Cu1—O1—C17	−82.6 (3)	C15'—C14—C15—C16	−84 (10)
N2—Cu1—O1—C17	−33.9 (3)	C14—C15—C16—C17	−8 (4)
C5—N1—C1—C2	−0.2 (7)	N3—C14—C15'—C16'	−25 (3)
Cu1—N1—C1—C2	178.7 (4)	C15—C14—C15'—C16'	63 (10)
N1—C1—C2—C3	0.0 (8)	C14—C15'—C16'—C17	34 (4)
C1—C2—C3—C4	−0.5 (9)	Cu1—O1—C17—N3	30.6 (5)
C2—C3—C4—C5	1.1 (9)	Cu1—O1—C17—C16	−145 (3)
C1—N1—C5—C4	0.9 (7)	Cu1—O1—C17—C16'	−153 (3)
Cu1—N1—C5—C4	−178.1 (4)	N2—N3—C17—O1	−8.0 (7)
C1—N1—C5—C6	177.1 (4)	C14—N3—C17—O1	−169.1 (5)
Cu1—N1—C5—C6	−1.9 (5)	N2—N3—C17—C16	169 (3)
C3—C4—C5—N1	−1.3 (8)	C14—N3—C17—C16	7 (3)
C3—C4—C5—C6	−177.2 (5)	N2—N3—C17—C16'	175 (3)
N3—N2—C6—C5	−179.2 (4)	C14—N3—C17—C16'	14 (3)
Cu1—N2—C6—C5	14.6 (5)	C15—C16—C17—O1	177.0 (18)

Experimental details

Crystal data
Chemical formula	[Cu(NCS)₂(C₁₆H₁₅N₃O)]
M_r	445.01
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	11.8883 (3), 13.3578 (3), 23.9669 (6)
β (°)	98.596 (1)
V (Å³)	3763.23 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.614, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7808, 4232, 3354
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.169, 1.16
No. of reflections	4232
No. of parameters	250
No. of restraints	3
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0468P)² + 21.4376P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.63

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

Selected bond lengths (Å) top

Cu1—O1	2.676 (4)	Cu1—N4	1.957 (4)
Cu1—N1	1.998 (4)	Cu1—N5	1.912 (4)
Cu1—N2	2.000 (3)

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kunnath, R. J., Prathapachandra Kurup, M. R. & Ng, S. W. (2012). Acta Cryst. E68, m1181. 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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