(1-{(E)-[Phen-yl(pyridin-2-yl-κN)methyl-idene]amino-κN}pyrrolidin-2-one-κO)bis-(thio-cyanato-κN)copper(II).

The Cu(II) atom in the title compound, [Cu(NCS)(2)(C(16)H(15)N(3)O)], is bonded to the N atoms of two thio-cyanate 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 inter-action. 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 n class="Chemical">Schiff base, see: Kunnath et al. (2012 ▶).

Experimental

Crystal data

[Cu(NCS)2(n class="Chemical">C16H15N3O)]

M = 445.01

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.169

S = 1.16

4232 reflections

250 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.63 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039918/xu5623sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039918/xu5623Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(NCS)2(C16H15N3O)]	F(000) = 1816
Mr = 445.01	Dx = 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

Bruker Kappa APEXII diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→15
Tmin = 0.614, Tmax = 1.000	k = −17→15
7808 measured reflections	l = −28→31

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(Fo2) + (0.0468P)2 + 21.4376P] where P = (Fo2 + 2Fc2)/3
4232 reflections	(Δ/σ)max = 0.001
250 parameters	Δρmax = 0.73 e Å−3
3 restraints	Δρmin = −0.63 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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)