Bis(acetato-κ2O,O′)(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)copper(II) monohydrate

Kaewthong, A.; Sukwattanasinitt, M.; Muangsin, N.

doi:10.1107/S1600536812020193

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m775

doi:10.1107/S1600536812020193

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Bis(acetato-κ²O,O′)(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)copper(II) monohydrate

Aphiwat Kaewthong,^a Mongkol Sukwattanasinitt ^a and Nongnuj Muangsin ^b ^*

^aCenter for Petroleum, Petrochemicals and Advanced Materials, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand, and ^bResearch Centre of Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand
^*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 17 April 2012; accepted 5 May 2012; online 16 May 2012)

In the title compound, [Cu(C₂H₃O₂)₂(C₁₂H₁₂N₂)₂]·H₂O, the Cu^II atom exhibits a distorted octahedral coordination geometry, defined by two N atoms from one 4,4′-dimethyl-2,2′-bipyridine ligand and four O atoms from two acetate ligands. In the crystal, O—H⋯O hydrogen bonds are observed between the coordinated carboxylate O atoms and the solvent water molecule.

Related literature

For related structures, see: Willett et al. (2001 ); Amani et al. (2009 ); Hojjat Kashani et al. (2008 ); Alizadeh et al. (2009 , 2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[Cu(C₂H₃O₂)₂(C₁₂H₁₂N₂)₂]·H₂O
M_r = 383.88
Orthorhombic, P b c n
a = 22.0667 (8) Å
b = 9.0192 (3) Å
c = 17.4088 (6) Å
V = 3464.8 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 296 K
0.48 × 0.43 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.544, T_max = 0.715
18193 measured reflections
4559 independent reflections
2835 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.172
S = 1.00
4559 reflections
229 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1S⋯O4ⁱ	0.80 (6)	2.12 (6)	2.878 (4)	158 (5)
O1S—H2S⋯O1ⁱⁱ	0.91 (7)	2.19 (7)	2.876 (4)	132 (6)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020193/jj2130sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020193/jj2130Isup2.hkl

checkCIF report

Comment top

The transition metal complexes of 4,4'-dimethyl-2,2'-bipyridine (4,4'-dmbipy) with various secondary types of ligands have been reported, for example, copper with bromide (Willett et al., 2001), iron with chloride (Amani et al., 2009), platinum with chloride (Hojjat Kashani et al., 2008), zinc with bromo (Alizadeh et al., 2010) and zinc with iodide (Alizadeh et al., 2009). Here, we report the title compound, [Cu(CH₃-bpy)(OAc)₂].H₂O, (I), a new copper complex with acetate ligands.

The asymmetric unit of the title compound, (I), is comprised of one water solvent molecule and a [Cu(CH₃-bpy)(OAc)₂] complex with a distorted octahedral arrangement around the mononuclear copper (II) group as evidenced by bond angles of N1—Cu1—N2[80.46 (10)^°], N1—Cu1—O3[94.27 (9)^°], O1—Cu1—O3[92.91 (10)^°], O1—Cu1—N2[92.41 (9)^°]. The six-coordinate geometry around the Cu (II) group is defined by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine ligand and four O atoms from two acetate ligands. Bond lengths and angles are within normal ranges (Allen et al., 1987). In the crystal structure, intermolecular O—H···O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms may help stabilize the structure.

Related literature top

For related structures, see: Willett et al. (2001); Amani et al. (2009); Hojjat Kashani et al. (2008); Alizadeh et al. (2009, 2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A solution of 4,4'-dimethyl-2,2'-bipyridine (17 mg, 0.1 mmol) and Cu(OAc)₂.H₂O (20 mg, 0.1 mmol) in ethanol (10 ml) was stirred and refluxed for 2 h. The solution was placed for slow evaporation at room temperature, and after two weeks X-ray quality crystals of Cu(CH₃-bpy)(OAc)₂ appeared as blue prisms. Yield: 23 mg, 60%.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound showing the atom labeling scheme of the asymmetric unit and 50% probability displacement ellipsoids.

Bis(acetato-κ²O,O')(4,4'-dimethyl-2,2'-bipyridine- κ²N,N')copper(II) monohydrate top

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₂H₁₂N₂)₂]·H₂O	F(000) = 1592
M_r = 383.88	D_x = 1.472 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4435 reflections
a = 22.0667 (8) Å	θ = 2.3–27.3°
b = 9.0192 (3) Å	µ = 1.29 mm⁻¹
c = 17.4088 (6) Å	T = 296 K
V = 3464.8 (2) Å³	Prism, blue
Z = 8	0.48 × 0.43 × 0.26 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4559 independent reflections
Radiation source: sealed X-ray tube	2835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.0°, θ_min = 2.3°
ϕ and ω scans	h = −29→27
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −12→12
T_min = 0.544, T_max = 0.715	l = −21→23
18193 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0896P)²] where P = (F_o² + 2F_c²)/3
4559 reflections	(Δ/σ)_max = 0.014
229 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₂H₁₂N₂)₂]·H₂O	V = 3464.8 (2) Å³
M_r = 383.88	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 22.0667 (8) Å	µ = 1.29 mm⁻¹
b = 9.0192 (3) Å	T = 296 K
c = 17.4088 (6) Å	0.48 × 0.43 × 0.26 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4559 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2835 reflections with I > 2σ(I)
T_min = 0.544, T_max = 0.715	R_int = 0.091
18193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.46 e Å⁻³
4559 reflections	Δρ_min = −0.87 e Å⁻³
229 parameters

Special details top

Experimental. IR [KBr, cm^-1]: 3426, 3100, 1608, 1444, 1118, 770, 621. HRMS (ESI): m/z 389 [M+Na]⁺.

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
C1	0.23138 (13)	0.3008 (3)	0.11076 (14)	0.0337 (6)
C2	0.25879 (12)	0.3929 (3)	0.04944 (14)	0.0339 (6)
C3	0.34865 (14)	0.4750 (3)	−0.00435 (16)	0.0448 (7)
H3	0.3908	0.4767	−0.0051	0.054*
C4	0.31721 (15)	0.5568 (3)	−0.05769 (16)	0.0456 (7)
H4	0.3384	0.6127	−0.0936	0.055*
C5	0.25498 (15)	0.5573 (3)	−0.05882 (14)	0.0412 (6)
C6	0.22514 (13)	0.4722 (3)	−0.00311 (15)	0.0379 (6)
H6	0.183	0.4693	−0.0016	0.046*
C7	0.21977 (17)	0.6439 (4)	−0.11742 (17)	0.0546 (9)
H7A	0.2403	0.7355	−0.1279	0.082*
H7B	0.18	0.6644	−0.0979	0.082*
H7C	0.2166	0.5871	−0.1639	0.082*
C8	0.17017 (14)	0.2973 (4)	0.12849 (15)	0.0404 (6)
H8	0.1434	0.3574	0.1015	0.049*
C9	0.14843 (14)	0.2055 (4)	0.18599 (17)	0.0428 (7)
C10	0.08269 (16)	0.2018 (5)	0.2063 (2)	0.0665 (10)
H10A	0.0642	0.2941	0.1921	0.1*
H10B	0.0783	0.1867	0.2606	0.1*
H10C	0.0633	0.1221	0.1792	0.1*
C11	0.19084 (14)	0.1170 (3)	0.22375 (16)	0.0421 (7)
H11	0.1782	0.0509	0.2615	0.051*
C12	0.25113 (14)	0.1271 (3)	0.20532 (16)	0.0422 (6)
H12	0.2787	0.0689	0.2323	0.051*
C13	0.44518 (14)	0.1966 (4)	0.02471 (18)	0.0472 (7)
C14	0.50052 (17)	0.2074 (5)	−0.0242 (2)	0.0669 (10)
H14A	0.5124	0.1101	−0.0407	0.1*
H14B	0.5328	0.2513	0.005	0.1*
H14C	0.492	0.2679	−0.0683	0.1*
C15	0.40175 (14)	0.1801 (4)	0.25884 (17)	0.0465 (7)
C16	0.4320 (2)	0.0955 (4)	0.3226 (2)	0.0695 (11)
H16A	0.4746	0.1167	0.3226	0.104*
H16B	0.4258	−0.0088	0.3151	0.104*
H16C	0.4148	0.1248	0.371	0.104*
N1	0.27219 (11)	0.2172 (3)	0.15003 (14)	0.0353 (5)
N2	0.32009 (11)	0.3924 (2)	0.04910 (12)	0.0369 (5)
O1	0.44010 (10)	0.2880 (3)	0.08035 (12)	0.0499 (5)
O1S	0.03896 (17)	1.0232 (4)	−0.12525 (17)	0.0744 (8)
H1S	0.062 (3)	1.080 (6)	−0.145 (3)	0.11 (2)*
H2S	0.003 (3)	1.064 (8)	−0.140 (4)	0.17 (3)*
O2	0.40469 (11)	0.1061 (3)	0.00996 (14)	0.0628 (6)
O3	0.38982 (10)	0.1081 (2)	0.19769 (12)	0.0512 (5)
O4	0.38908 (14)	0.3131 (3)	0.26600 (15)	0.0721 (8)
Cu1	0.359174 (16)	0.24915 (3)	0.122075 (19)	0.03621 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0374 (15)	0.0331 (13)	0.0306 (12)	0.0006 (11)	−0.0018 (10)	−0.0027 (11)
C2	0.0383 (15)	0.0319 (13)	0.0315 (13)	0.0038 (10)	0.0012 (11)	−0.0039 (10)
C3	0.0423 (16)	0.0437 (16)	0.0482 (17)	−0.0031 (13)	0.0049 (13)	0.0047 (13)
C4	0.0516 (19)	0.0430 (17)	0.0422 (15)	−0.0043 (12)	0.0065 (13)	0.0064 (12)
C5	0.0577 (19)	0.0337 (14)	0.0321 (13)	0.0085 (11)	0.0003 (13)	−0.0005 (11)
C6	0.0361 (15)	0.0401 (15)	0.0376 (14)	0.0067 (11)	0.0016 (11)	−0.0004 (12)
C7	0.072 (2)	0.0497 (19)	0.0425 (17)	0.0115 (16)	−0.0060 (14)	0.0082 (14)
C8	0.0360 (16)	0.0460 (15)	0.0393 (15)	0.0019 (13)	−0.0026 (12)	−0.0010 (12)
C9	0.0431 (17)	0.0462 (15)	0.0392 (16)	−0.0104 (12)	0.0023 (12)	−0.0018 (13)
C10	0.042 (2)	0.088 (3)	0.070 (2)	−0.0099 (18)	0.0070 (17)	0.019 (2)
C11	0.0495 (18)	0.0436 (16)	0.0332 (13)	−0.0080 (13)	0.0008 (12)	0.0018 (12)
C12	0.0500 (18)	0.0403 (15)	0.0362 (14)	0.0007 (12)	−0.0036 (13)	0.0051 (11)
C13	0.0342 (16)	0.0573 (18)	0.0501 (17)	0.0060 (14)	−0.0013 (13)	0.0084 (15)
C14	0.050 (2)	0.079 (2)	0.072 (2)	0.0076 (18)	0.0164 (18)	0.008 (2)
C15	0.0403 (17)	0.056 (2)	0.0436 (16)	0.0002 (14)	−0.0090 (13)	0.0072 (14)
C16	0.077 (3)	0.072 (2)	0.060 (2)	0.0003 (19)	−0.0247 (19)	0.0156 (19)
N1	0.0384 (13)	0.0371 (12)	0.0305 (11)	0.0022 (9)	−0.0003 (10)	0.0011 (9)
N2	0.0348 (12)	0.0389 (12)	0.0371 (12)	0.0010 (9)	0.0012 (9)	0.0013 (10)
O1	0.0354 (12)	0.0657 (13)	0.0487 (13)	0.0004 (10)	−0.0037 (9)	0.0006 (11)
O1S	0.065 (2)	0.0660 (18)	0.092 (2)	0.0099 (15)	0.0102 (16)	0.0145 (16)
O2	0.0445 (13)	0.0694 (16)	0.0743 (16)	−0.0041 (11)	0.0014 (12)	−0.0130 (12)
O3	0.0515 (13)	0.0535 (13)	0.0486 (12)	0.0073 (10)	−0.0124 (10)	0.0020 (10)
O4	0.087 (2)	0.0588 (15)	0.0709 (16)	0.0163 (15)	−0.0301 (14)	−0.0092 (14)
Cu1	0.0334 (2)	0.0398 (3)	0.0354 (2)	0.00240 (13)	−0.00412 (13)	−0.00033 (13)

Geometric parameters (Å, º) top

C1—N1	1.359 (4)	C11—C12	1.372 (4)
C1—C8	1.386 (4)	C11—H11	0.93
C1—C2	1.482 (4)	C12—N1	1.343 (4)
C2—N2	1.353 (3)	C12—H12	0.93
C2—C6	1.378 (4)	C13—O2	1.237 (4)
C3—N2	1.349 (3)	C13—O1	1.277 (4)
C3—C4	1.374 (4)	C13—C14	1.492 (5)
C3—H3	0.93	C14—H14A	0.96
C4—C5	1.373 (5)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—C6	1.401 (4)	C15—O4	1.238 (4)
C5—C7	1.501 (4)	C15—O3	1.275 (4)
C6—H6	0.93	C15—C16	1.504 (4)
C7—H7A	0.96	C16—H16A	0.96
C7—H7B	0.96	C16—H16B	0.96
C7—H7C	0.96	C16—H16C	0.96
C8—C9	1.385 (4)	N1—Cu1	2.001 (2)
C8—H8	0.93	N2—Cu1	2.007 (2)
C9—C11	1.395 (4)	O1—Cu1	1.959 (2)
C9—C10	1.493 (5)	O1S—H1S	0.80 (6)
C10—H10A	0.96	O1S—H2S	0.91 (7)
C10—H10B	0.96	O3—Cu1	1.952 (2)
C10—H10C	0.96

N1—C1—C8	121.4 (3)	C9—C11—H11	119.9
N1—C1—C2	113.8 (2)	N1—C12—C11	122.9 (3)
C8—C1—C2	124.8 (3)	N1—C12—H12	118.5
N2—C2—C6	122.5 (2)	C11—C12—H12	118.5
N2—C2—C1	114.2 (2)	O2—C13—O1	121.3 (3)
C6—C2—C1	123.3 (3)	O2—C13—C14	121.1 (3)
N2—C3—C4	121.8 (3)	O1—C13—C14	117.5 (3)
N2—C3—H3	119.1	C13—C14—H14A	109.5
C4—C3—H3	119.1	C13—C14—H14B	109.5
C5—C4—C3	121.1 (3)	H14A—C14—H14B	109.5
C5—C4—H4	119.4	C13—C14—H14C	109.5
C3—C4—H4	119.4	H14A—C14—H14C	109.5
C4—C5—C6	117.3 (2)	H14B—C14—H14C	109.5
C4—C5—C7	121.9 (3)	O4—C15—O3	122.1 (3)
C6—C5—C7	120.8 (3)	O4—C15—C16	121.2 (3)
C2—C6—C5	119.4 (3)	O3—C15—C16	116.8 (3)
C2—C6—H6	120.3	C15—C16—H16A	109.5
C5—C6—H6	120.3	C15—C16—H16B	109.5
C5—C7—H7A	109.5	H16A—C16—H16B	109.5
C5—C7—H7B	109.5	C15—C16—H16C	109.5
H7A—C7—H7B	109.5	H16A—C16—H16C	109.5
C5—C7—H7C	109.5	H16B—C16—H16C	109.5
H7A—C7—H7C	109.5	C12—N1—C1	117.9 (3)
H7B—C7—H7C	109.5	C12—N1—Cu1	126.4 (2)
C9—C8—C1	120.8 (3)	C1—N1—Cu1	115.70 (19)
C9—C8—H8	119.6	C3—N2—C2	117.9 (2)
C1—C8—H8	119.6	C3—N2—Cu1	126.3 (2)
C8—C9—C11	116.8 (3)	C2—N2—Cu1	115.43 (16)
C8—C9—C10	121.4 (3)	C13—O1—Cu1	104.23 (19)
C11—C9—C10	121.8 (3)	H1S—O1S—H2S	100 (5)
C9—C10—H10A	109.5	C15—O3—Cu1	107.6 (2)
C9—C10—H10B	109.5	O3—Cu1—O1	92.91 (10)
H10A—C10—H10B	109.5	O3—Cu1—N1	94.27 (9)
C9—C10—H10C	109.5	O1—Cu1—N1	171.94 (9)
H10A—C10—H10C	109.5	O3—Cu1—N2	174.64 (9)
H10B—C10—H10C	109.5	O1—Cu1—N2	92.41 (9)
C12—C11—C9	120.2 (3)	N1—Cu1—N2	80.46 (10)
C12—C11—H11	119.9

N1—C1—C2—N2	−7.7 (3)	C2—C1—N1—Cu1	4.5 (3)
C8—C1—C2—N2	172.0 (3)	C4—C3—N2—C2	−0.6 (4)
N1—C1—C2—C6	172.1 (2)	C4—C3—N2—Cu1	172.2 (2)
C8—C1—C2—C6	−8.2 (4)	C6—C2—N2—C3	1.0 (4)
N2—C3—C4—C5	−0.2 (4)	C1—C2—N2—C3	−179.2 (2)
C3—C4—C5—C6	0.5 (4)	C6—C2—N2—Cu1	−172.5 (2)
C3—C4—C5—C7	−179.0 (3)	C1—C2—N2—Cu1	7.3 (3)
N2—C2—C6—C5	−0.7 (4)	O2—C13—O1—Cu1	−2.6 (4)
C1—C2—C6—C5	179.5 (2)	C14—C13—O1—Cu1	174.6 (3)
C4—C5—C6—C2	−0.1 (4)	O4—C15—O3—Cu1	6.1 (4)
C7—C5—C6—C2	179.4 (3)	C16—C15—O3—Cu1	−174.1 (3)
N1—C1—C8—C9	−1.5 (4)	C15—O3—Cu1—O1	90.9 (2)
C2—C1—C8—C9	178.8 (3)	C15—O3—Cu1—N1	−92.8 (2)
C1—C8—C9—C11	−0.7 (4)	C13—O1—Cu1—O3	92.8 (2)
C1—C8—C9—C10	179.4 (3)	C13—O1—Cu1—N2	−87.8 (2)
C8—C9—C11—C12	2.3 (4)	C12—N1—Cu1—O3	1.4 (2)
C10—C9—C11—C12	−177.8 (3)	C1—N1—Cu1—O3	178.4 (2)
C9—C11—C12—N1	−1.8 (4)	C12—N1—Cu1—N2	−177.6 (2)
C11—C12—N1—C1	−0.4 (4)	C1—N1—Cu1—N2	−0.6 (2)
C11—C12—N1—Cu1	176.5 (2)	C3—N2—Cu1—O1	−0.5 (2)
C8—C1—N1—C12	2.1 (4)	C2—N2—Cu1—O1	172.35 (18)
C2—C1—N1—C12	−178.2 (2)	C3—N2—Cu1—N1	−176.8 (2)
C8—C1—N1—Cu1	−175.2 (2)	C2—N2—Cu1—N1	−3.87 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O4ⁱ	0.80 (6)	2.12 (6)	2.878 (4)	158 (5)
O1S—H2S···O1ⁱⁱ	0.91 (7)	2.19 (7)	2.876 (4)	132 (6)

Symmetry codes: (i) −x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃O₂)₂(C₁₂H₁₂N₂)₂]·H₂O
M_r	383.88
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	22.0667 (8), 9.0192 (3), 17.4088 (6)
V (Å³)	3464.8 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.48 × 0.43 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.544, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	18193, 4559, 2835
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.172, 1.00
No. of reflections	4559
No. of parameters	229
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.87

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O4ⁱ	0.80 (6)	2.12 (6)	2.878 (4)	158 (5)
O1S—H2S···O1ⁱⁱ	0.91 (7)	2.19 (7)	2.876 (4)	132 (6)

Symmetry codes: (i) −x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, −z.

Acknowledgements

This work was supported by the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphisek Somphot Endowment Fund) to AK, the National Research University Project of CHE and the Ratchadaphiseksomphot Endowment Fund (FW657B) to NM, the Thai Government Stimulus Package 2 (TKK2555) under the Project for Establishment of Comprehensive Center for Innovative Food, Health Products and Agrigulture and Center for Petroleum Petrochemicals and Advanced Materials.

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