Dichlorido(1-{(E)-[phen­yl(pyridin-2-yl-κN)methyl­idene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate

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

doi:10.1107/S1600536812035398

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1181

doi:10.1107/S1600536812035398

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Dichlorido(1-{(E)-[phenyl(pyridin-2-yl-κN)methylidene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate

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 3 August 2012; accepted 10 August 2012; online 23 August 2012)

The Cu^II atom in the title compound, [CuCl₂(C₁₆H₁₅N₃O)]·H₂O, 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 molecules, the interaction generating a centrosymmetric dimer through a cyclic R₄²(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_r = 417.77
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.076
S = 1.07
3987 reflections
225 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+1, -y+1, -z+1.

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: 10.1107/S1600536812035398/zs2227sup1.cif

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

checkCIF report

Comment top

Among the plethora of Schiff bases that have been synthesized for the purpose of furnishing coordination compounds, some are synthesized in situ, and their formulation is inferred from the crystal structure of the product. Phenyl[(pyridin-2-yl)methylidene]amino]pyrrolidin-2-one is an example of such a Schiff base, which possess a carbonyl group and it forms a monohydrated complex with copper(II) chloride (Scheme I, Fig. 1). The Cu^II atom in this complex is N,N',O-chelated by the neutral Schiff ligand and has a square-pyramidal geometry, with the atom displaced out of the square plane in the direction of the apical Cl atom by 0.316 (1) Å. The apical Cl atoms of adjacent complex units are hydrogen-bond acceptors to two water molecules (Table 1), the interaction generating a centrosymmetric dimer (Fig. 2) through a cyclic R²₄(8) association (Etter et al., 1990).

Related literature top

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

Experimental top

1-[(E)-[Phenyl(pyridin-2-yl)methylidene]amino]pyrrolidin-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 in methanol for 2 h. Copper(II) chloride dihydrate (0.170 g, 1 mmol) was added, and the mixture heated for 5 h. The resulting pale green solid was collected and recrystallized from methanol.

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 [CuCl₂(C₁₆H₁₅N₃O)]^.H₂O at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The hydrogen-bonded dimer.

Dichlorido(1-{(E)-[phenyl(pyridin-2-yl- κN)methylidene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate top

Crystal data top

[CuCl₂(C₁₆H₁₅N₃O)]·H₂O	Z = 2
M_r = 417.77	F(000) = 426
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.026	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(F_o²) + (0.0379P)² + 0.3259P] where P = (F_o² + 2F_c²)/3
3987 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.45 e Å⁻³
2 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[CuCl₂(C₁₆H₁₅N₃O)]·H₂O	γ = 105.4911 (6)°
M_r = 417.77	V = 870.84 (3) Å³
Triclinic, P1	Z = 2
a = 9.1289 (2) Å	Mo Kα radiation
b = 9.4017 (2) Å	µ = 1.57 mm⁻¹
c = 10.6798 (2) Å	T = 293 K
α = 90.4349 (6)°	0.30 × 0.30 × 0.30 mm
β = 99.1627 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3987 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3761 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.650	R_int = 0.033
14839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	2 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.45 e Å⁻³
3987 reflections	Δρ_min = −0.34 e Å⁻³
225 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₆H₁₅N₃O)]·H₂O
M_r	417.77
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1289 (2), 9.4017 (2), 10.6798 (2)
α, β, γ (°)	90.4349 (6), 99.1627 (6), 105.4911 (6)
V (Å³)	870.84 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.650, 0.650
No. of measured, independent and observed [I > 2σ(I)] reflections	14839, 3987, 3761
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.076, 1.07
No. of reflections	3987
No. of parameters	225
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.34

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

RJK thanks the University Grants Commission (India) for a Junior Research Fellowship. We thank the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, for the diffraction measurements. We also thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) 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
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science 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
Tidwell, T. T. (2008). Angew. Chem. Int. Ed. Engl. 47, 1016–1020. Web of Science CrossRef PubMed CAS 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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Volume 68| Part 9| September 2012| Page m1181

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chlorido(1-{(E)-[phen­yl(pyridin-2-yl-κN)methyl­­idene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichlorido(1-{(E)-[phenyl(pyridin-2-yl-κN)methylidene]amino-κN}pyrrolidin-2-one-κO)copper(II) monohydrate