Bis(acetato-κ(2)O,O')(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')copper(II) monohydrate.

In the title compound, [Cu(C(2)H(3)O(2))(2)(C(12)H(12)N(2))(2)]·H(2)O, the Cu(II) atom exhibits a distorted octa-hedral 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 carboxyl-ate O atoms and the solvent water mol-ecule.

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 = 383.88

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.172

S = 1.00

4559 reflections

229 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.87 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020193/jj2130sup1.cif

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

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

[Cu(C2H3O2)2(C12H12N2)2]·H2O	F(000) = 1592
Mr = 383.88	Dx = 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

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

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(Fo2) + (0.0896P)2] where P = (Fo2 + 2Fc2)/3
4559 reflections	(Δ/σ)max = 0.014
229 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.87 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) ; (ii) .