Dichlorido(1-{(E)-[phen-yl(pyridin-2-yl-κN)methyl-idene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate.

The Cu(II) atom in the title compound, [CuCl(2)(C(16)H(15)N(3)O)]·H(2)O, is N,N',O-chelated by the neutral Schiff base ligand and exists in a square-pyramidal geometry. It is displaced by 0.316 (1) Å out of the square plane (r.m.s. deviation = 0.015 Å) in the direction of the apical Cl atom. The apical Cl atoms of adjacent complex units are hydrogen-bond acceptors to two water mol-ecules, the inter-action generating a centrosymmetric dimer through a cyclic R(4) (2)(8) association.

Related literature

For a history of Schiff bases, see: Tidwell (2008 ▶). For graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

[CuCl2(C16H15N3O)]·H2O

M = 417.77

Triclinic,

a = 9.1289 (2) Å

b = 9.4017 (2) Å

c = 10.6798 (2) Å

α = 90.4349 (6)°

β = 99.1627 (6)°

γ = 105.4911 (6)°

V = 870.84 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.57 mm−1

T = 293 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.650, T max = 0.650

14839 measured reflections

3987 independent reflections

3761 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.076

S = 1.07

3987 reflections

225 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.34 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/S1600536812035398/zs2227sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035398/zs2227Isup2.hkl

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

[CuCl2(C16H15N3O)]·H2O	Z = 2
Mr = 417.77	F(000) = 426
Triclinic, P1	Dx = 1.593 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1289 (2) Å	Cell parameters from 9988 reflections
b = 9.4017 (2) Å	θ = 2.3–28.2°
c = 10.6798 (2) Å	µ = 1.57 mm−1
α = 90.4349 (6)°	T = 293 K
β = 99.1627 (6)°	Cube, green
γ = 105.4911 (6)°	0.30 × 0.30 × 0.30 mm
V = 870.84 (3) Å3

Bruker Kappa APEXII CCD diffractometer	3987 independent reflections
Radiation source: fine-focus sealed tube	3761 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.650, Tmax = 0.650	k = −12→12
14839 measured reflections	l = −13→13

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.45 e Å−3
2 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.48709 (2)	0.63969 (2)	0.845334 (18)	0.03229 (8)
Cl1	0.54227 (8)	0.72830 (6)	0.64075 (5)	0.06303 (16)
Cl2	0.64240 (5)	0.82061 (5)	0.97595 (4)	0.04703 (12)
O1	0.62811 (14)	0.49646 (15)	0.86442 (14)	0.0478 (3)
O1W	0.2859 (2)	0.5064 (3)	0.4420 (2)	0.0832 (6)
N1	0.28316 (15)	0.68570 (15)	0.84571 (13)	0.0340 (3)
N2	0.33922 (15)	0.44928 (14)	0.77515 (13)	0.0308 (3)
N3	0.40965 (15)	0.34475 (15)	0.75166 (14)	0.0339 (3)
C1	0.2610 (2)	0.81241 (19)	0.88367 (18)	0.0410 (4)
H1A	0.3462	0.8893	0.9176	0.049*
C2	0.1151 (2)	0.8336 (2)	0.8743 (2)	0.0505 (5)
H2A	0.1028	0.9227	0.9030	0.061*
C3	−0.0106 (2)	0.7216 (2)	0.8222 (2)	0.0557 (5)
H3	−0.1094	0.7339	0.8150	0.067*
C4	0.0108 (2)	0.5900 (2)	0.7803 (2)	0.0467 (4)
H4	−0.0729	0.5129	0.7439	0.056*
C5	0.15940 (18)	0.57554 (17)	0.79400 (16)	0.0333 (3)
C6	0.19396 (18)	0.43781 (17)	0.75440 (15)	0.0320 (3)
C7	0.06742 (18)	0.30651 (17)	0.70149 (17)	0.0342 (3)
C8	0.0047 (3)	0.2941 (2)	0.5739 (2)	0.0549 (5)
H8	0.0428	0.3672	0.5202	0.066*
C9	−0.1152 (3)	0.1720 (3)	0.5270 (2)	0.0704 (7)
H9	−0.1575	0.1632	0.4412	0.085*
C10	−0.1720 (2)	0.0643 (2)	0.6054 (3)	0.0614 (6)
H10	−0.2518	−0.0179	0.5726	0.074*
C11	−0.1118 (2)	0.0772 (2)	0.7324 (2)	0.0530 (5)
H11	−0.1516	0.0041	0.7856	0.064*
C12	0.0085 (2)	0.1990 (2)	0.7818 (2)	0.0428 (4)
H12	0.0491	0.2082	0.8680	0.051*
C13	0.3480 (2)	0.19716 (19)	0.68807 (18)	0.0399 (4)
H13A	0.2971	0.2019	0.6019	0.048*
H13B	0.2759	0.1326	0.7344	0.048*
C14	0.4930 (2)	0.1453 (2)	0.6898 (2)	0.0510 (5)
H14A	0.4770	0.0461	0.7198	0.061*
H14B	0.5182	0.1444	0.6049	0.061*
C15	0.6226 (2)	0.2524 (2)	0.7783 (2)	0.0509 (5)
H15A	0.6500	0.2064	0.8563	0.061*
H15B	0.7132	0.2849	0.7382	0.061*
C16	0.5608 (2)	0.3787 (2)	0.80431 (18)	0.0392 (4)
H1	0.355 (3)	0.564 (3)	0.493 (3)	0.100 (12)*
H2	0.330 (4)	0.441 (3)	0.435 (4)	0.114 (15)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02431 (11)	0.02906 (11)	0.03759 (12)	0.00025 (8)	0.00019 (7)	−0.00478 (8)
Cl1	0.0821 (4)	0.0500 (3)	0.0433 (3)	−0.0090 (3)	0.0168 (2)	0.0018 (2)
Cl2	0.0366 (2)	0.0455 (2)	0.0467 (2)	−0.00346 (18)	−0.00297 (17)	−0.01499 (18)
O1	0.0300 (6)	0.0431 (7)	0.0650 (9)	0.0087 (5)	−0.0048 (6)	−0.0102 (6)
O1W	0.0539 (11)	0.1031 (17)	0.0784 (13)	0.0071 (11)	−0.0049 (9)	−0.0176 (12)
N1	0.0284 (6)	0.0284 (6)	0.0404 (7)	0.0027 (5)	0.0005 (5)	−0.0031 (5)
N2	0.0270 (6)	0.0253 (6)	0.0374 (7)	0.0043 (5)	0.0027 (5)	−0.0006 (5)
N3	0.0292 (6)	0.0277 (6)	0.0426 (7)	0.0055 (5)	0.0039 (5)	−0.0018 (5)
C1	0.0379 (9)	0.0302 (8)	0.0495 (10)	0.0047 (7)	−0.0003 (7)	−0.0060 (7)
C2	0.0452 (10)	0.0355 (9)	0.0704 (13)	0.0149 (8)	0.0020 (9)	−0.0109 (9)
C3	0.0357 (9)	0.0442 (10)	0.0866 (16)	0.0148 (8)	0.0026 (10)	−0.0097 (10)
C4	0.0281 (8)	0.0363 (9)	0.0696 (12)	0.0042 (7)	−0.0010 (8)	−0.0078 (8)
C5	0.0274 (7)	0.0270 (7)	0.0409 (8)	0.0024 (6)	0.0011 (6)	−0.0019 (6)
C6	0.0281 (7)	0.0272 (7)	0.0357 (8)	0.0016 (6)	0.0013 (6)	−0.0006 (6)
C7	0.0244 (7)	0.0259 (7)	0.0487 (9)	0.0030 (6)	0.0022 (6)	−0.0033 (6)
C8	0.0518 (12)	0.0488 (11)	0.0482 (11)	−0.0085 (9)	0.0008 (9)	−0.0049 (9)
C9	0.0602 (14)	0.0709 (16)	0.0591 (14)	−0.0100 (12)	−0.0031 (11)	−0.0230 (12)
C10	0.0396 (10)	0.0414 (11)	0.0903 (17)	−0.0088 (8)	0.0091 (10)	−0.0261 (11)
C11	0.0368 (9)	0.0295 (8)	0.0926 (16)	0.0040 (7)	0.0193 (10)	0.0060 (9)
C12	0.0334 (8)	0.0344 (8)	0.0578 (11)	0.0056 (7)	0.0058 (7)	0.0058 (7)
C13	0.0404 (9)	0.0314 (8)	0.0460 (9)	0.0073 (7)	0.0060 (7)	−0.0074 (7)
C14	0.0479 (11)	0.0396 (10)	0.0684 (13)	0.0156 (8)	0.0119 (9)	−0.0043 (9)
C15	0.0423 (10)	0.0509 (11)	0.0632 (12)	0.0225 (9)	0.0033 (9)	−0.0043 (9)
C16	0.0321 (8)	0.0392 (9)	0.0461 (9)	0.0102 (7)	0.0048 (7)	0.0014 (7)

Cu1—N2	1.9888 (13)	C5—C6	1.486 (2)
Cu1—N1	2.0213 (14)	C6—C7	1.482 (2)
Cu1—O1	2.0878 (13)	C7—C8	1.382 (3)
Cu1—Cl2	2.2125 (4)	C7—C12	1.384 (2)
Cu1—Cl1	2.4240 (5)	C8—C9	1.383 (3)
O1—C16	1.231 (2)	C8—H8	0.9300
O1W—H1	0.834 (10)	C9—C10	1.366 (4)
O1W—H2	0.833 (10)	C9—H9	0.9300
N1—C1	1.331 (2)	C10—C11	1.372 (4)
N1—C5	1.350 (2)	C10—H10	0.9300
N2—C6	1.284 (2)	C11—C12	1.389 (3)
N2—N3	1.3518 (19)	C11—H11	0.9300
N3—C16	1.355 (2)	C12—H12	0.9300
N3—C13	1.466 (2)	C13—C14	1.526 (3)
C1—C2	1.387 (3)	C13—H13A	0.9700
C1—H1A	0.9300	C13—H13B	0.9700
C2—C3	1.371 (3)	C14—C15	1.517 (3)
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.385 (3)	C14—H14B	0.9700
C3—H3	0.9300	C15—C16	1.486 (2)
C4—C5	1.384 (2)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
N2—Cu1—N1	78.77 (5)	C8—C7—C12	120.20 (17)
N2—Cu1—O1	78.29 (5)	C8—C7—C6	120.33 (16)
N1—Cu1—O1	152.34 (6)	C12—C7—C6	119.42 (16)
N2—Cu1—Cl2	163.34 (4)	C7—C8—C9	119.4 (2)
N1—Cu1—Cl2	100.41 (4)	C7—C8—H8	120.3
O1—Cu1—Cl2	97.17 (4)	C9—C8—H8	120.3
N2—Cu1—Cl1	95.08 (4)	C10—C9—C8	120.6 (2)
N1—Cu1—Cl1	100.24 (4)	C10—C9—H9	119.7
O1—Cu1—Cl1	96.99 (5)	C8—C9—H9	119.7
Cl2—Cu1—Cl1	101.40 (2)	C9—C10—C11	120.19 (19)
C16—O1—Cu1	109.91 (11)	C9—C10—H10	119.9
H1—O1W—H2	98 (3)	C11—C10—H10	119.9
C1—N1—C5	118.68 (14)	C10—C11—C12	120.2 (2)
C1—N1—Cu1	127.24 (12)	C10—C11—H11	119.9
C5—N1—Cu1	113.95 (11)	C12—C11—H11	119.9
C6—N2—N3	127.33 (14)	C7—C12—C11	119.36 (19)
C6—N2—Cu1	119.74 (11)	C7—C12—H12	120.3
N3—N2—Cu1	112.90 (10)	C11—C12—H12	120.3
N2—N3—C16	113.89 (13)	N3—C13—C14	102.37 (15)
N2—N3—C13	131.06 (14)	N3—C13—H13A	111.3
C16—N3—C13	114.85 (14)	C14—C13—H13A	111.3
N1—C1—C2	122.22 (16)	N3—C13—H13B	111.3
N1—C1—H1A	118.9	C14—C13—H13B	111.3
C2—C1—H1A	118.9	H13A—C13—H13B	109.2
C3—C2—C1	119.11 (17)	C15—C14—C13	107.37 (15)
C3—C2—H2A	120.4	C15—C14—H14A	110.2
C1—C2—H2A	120.4	C13—C14—H14A	110.2
C2—C3—C4	119.32 (18)	C15—C14—H14B	110.2
C2—C3—H3	120.3	C13—C14—H14B	110.2
C4—C3—H3	120.3	H14A—C14—H14B	108.5
C5—C4—C3	118.56 (17)	C16—C15—C14	105.17 (15)
C5—C4—H4	120.7	C16—C15—H15A	110.7
C3—C4—H4	120.7	C14—C15—H15A	110.7
N1—C5—C4	122.09 (15)	C16—C15—H15B	110.7
N1—C5—C6	115.32 (14)	C14—C15—H15B	110.7
C4—C5—C6	122.59 (15)	H15A—C15—H15B	108.8
N2—C6—C7	127.44 (14)	O1—C16—N3	122.62 (16)
N2—C6—C5	112.02 (13)	O1—C16—C15	128.59 (17)
C7—C6—C5	120.52 (13)	N3—C16—C15	108.77 (15)
N2—Cu1—O1—C16	12.11 (13)	C3—C4—C5—C6	178.79 (19)
N1—Cu1—O1—C16	46.6 (2)	N3—N2—C6—C7	1.0 (3)
Cl2—Cu1—O1—C16	175.86 (13)	Cu1—N2—C6—C7	179.23 (13)
Cl1—Cu1—O1—C16	−81.66 (13)	N3—N2—C6—C5	179.28 (14)
N2—Cu1—N1—C1	−179.79 (16)	Cu1—N2—C6—C5	−2.54 (19)
O1—Cu1—N1—C1	145.74 (15)	N1—C5—C6—N2	−1.0 (2)
Cl2—Cu1—N1—C1	17.15 (16)	C4—C5—C6—N2	179.64 (17)
Cl1—Cu1—N1—C1	−86.58 (15)	N1—C5—C6—C7	177.33 (15)
N2—Cu1—N1—C5	−3.96 (12)	C4—C5—C6—C7	−2.0 (3)
O1—Cu1—N1—C5	−38.43 (19)	N2—C6—C7—C8	−97.6 (2)
Cl2—Cu1—N1—C5	−167.02 (11)	C5—C6—C7—C8	84.3 (2)
Cl1—Cu1—N1—C5	89.24 (12)	N2—C6—C7—C12	84.8 (2)
N1—Cu1—N2—C6	3.67 (13)	C5—C6—C7—C12	−93.27 (19)
O1—Cu1—N2—C6	168.11 (14)	C12—C7—C8—C9	−1.3 (3)
Cl2—Cu1—N2—C6	92.48 (18)	C6—C7—C8—C9	−178.8 (2)
Cl1—Cu1—N2—C6	−95.78 (13)	C7—C8—C9—C10	0.2 (4)
N1—Cu1—N2—N3	−177.89 (12)	C8—C9—C10—C11	0.8 (4)
O1—Cu1—N2—N3	−13.46 (11)	C9—C10—C11—C12	−0.7 (3)
Cl2—Cu1—N2—N3	−89.09 (17)	C8—C7—C12—C11	1.4 (3)
Cl1—Cu1—N2—N3	82.65 (11)	C6—C7—C12—C11	178.96 (16)
C6—N2—N3—C16	−168.57 (16)	C10—C11—C12—C7	−0.4 (3)
Cu1—N2—N3—C16	13.14 (17)	N2—N3—C13—C14	177.20 (17)
C6—N2—N3—C13	5.9 (3)	C16—N3—C13—C14	−8.4 (2)
Cu1—N2—N3—C13	−172.38 (14)	N3—C13—C14—C15	11.8 (2)
C5—N1—C1—C2	1.4 (3)	C13—C14—C15—C16	−11.4 (2)
Cu1—N1—C1—C2	177.05 (15)	Cu1—O1—C16—N3	−9.2 (2)
N1—C1—C2—C3	−1.2 (3)	Cu1—O1—C16—C15	172.06 (17)
C1—C2—C3—C4	0.1 (4)	N2—N3—C16—O1	−2.2 (3)
C2—C3—C4—C5	0.7 (3)	C13—N3—C16—O1	−177.64 (17)
C1—N1—C5—C4	−0.5 (3)	N2—N3—C16—C15	176.76 (15)
Cu1—N1—C5—C4	−176.76 (15)	C13—N3—C16—C15	1.4 (2)
C1—N1—C5—C6	−179.87 (15)	C14—C15—C16—O1	−174.7 (2)
Cu1—N1—C5—C6	3.92 (18)	C14—C15—C16—N3	6.4 (2)
C3—C4—C5—N1	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···Cl1	0.83 (1)	2.34 (1)	3.175 (2)	178 (4)
O1w—H2···Cl1i	0.83 (1)	2.41 (2)	3.221 (3)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯Cl1	0.83 (1)	2.34 (1)	3.175 (2)	178 (4)
O1w—H2⋯Cl1i	0.83 (1)	2.41 (2)	3.221 (3)	165 (4)

Symmetry code: (i) .