Bis(μ-2-phenyl-acetato-κO:O)bis-[(2,2'-bipyridyl-κN,N')(2-phenyl-acetato-κO)copper(II)] dihydrate.

The mol-ecule of the binuclear title complex, [Cu(2)(C(8)H(7)O(2))(4)(C(10)H(8)N(2))(2)]·2H(2)O, is located on an inversion centre. The Cu atoms are bridged by two O atoms of the monodentate phenyl-acetate groups [Cu-O = 1.9808 (14) and 2.3668 (14) Å]. The longer of the two bridging Cu-O bonds takes the apical position of the distorted square-pyramidal environment of the Cu atom, which is completed by two N atoms of the chelate 2,2'-bipyridine ligand [Cu-N = 2.0107 (17) and 2.0234 (16) Å]. The mol-ecules are assembled into stacks along [100] through π-π inter-actions with inter-planar distances of 3.630 (4) and 3.407 (3) Å; the resulting stacks are further connected into a three-dimensional supra-molecular architecture by O-H⋯O and C-H⋯O hydrogen-bonding inter-actions.

Related literature

For applications of inorganic–organic hybrid materials, see: Pan et al. (2003 ▶); Shibasaki & Yoshikawa (2002 ▶). For related structures, see: Addison & Rao (1984 ▶); Antolini et al. (1985 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

[Cu2(C8H7n class="Chemical">O2)4(C10H8N2)2]·2H2O

M = 1016.02

Monoclinic,

a = 10.213 (2) Å

b = 16.058 (3) Å

c = 14.633 (3) Å

β = 100.75 (3)°

V = 2357.7 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.97 mm−1

T = 295 K

0.17 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.678, T max = 0.784

22348 measured reflections

5356 independent reflections

4268 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.10

5356 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.56 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035483/ya2144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035483/ya2144Isup2.hkl

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

[Cu2(C8H7O2)4(C10H8N2)2]·2H2O	F(000) = 1052
Mr = 1016.02	Dx = 1.431 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 22348 reflections
a = 10.213 (2) Å	θ = 3.1–27.4°
b = 16.058 (3) Å	µ = 0.97 mm−1
c = 14.633 (3) Å	T = 295 K
β = 100.75 (3)°	Block, blue
V = 2357.7 (8) Å3	0.17 × 0.14 × 0.11 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	5356 independent reflections
Radiation source: fine-focus sealed tube	4268 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −20→20
Tmin = 0.678, Tmax = 0.784	l = −18→18
22348 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0357P)2 + 1.1037P] where P = (Fo2 + 2Fc2)/3
5356 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
Cu	0.34936 (2)	0.003603 (15)	0.032956 (16)	0.03079 (8)
O1	0.51708 (12)	0.08258 (8)	−0.01885 (10)	0.0349 (3)
O2	0.65975 (14)	0.18355 (10)	−0.03382 (12)	0.0509 (4)
C1	0.54722 (19)	0.15958 (13)	−0.02762 (13)	0.0335 (4)
C2	0.4344 (2)	0.22176 (13)	−0.03118 (15)	0.0390 (5)
H2A	0.3904	0.2116	0.0211	0.047*
H2B	0.4716	0.2775	−0.0244	0.047*
C3	0.33151 (19)	0.21773 (12)	−0.12042 (15)	0.0371 (4)
C4	0.3645 (3)	0.18987 (17)	−0.20253 (17)	0.0583 (7)
H4A	0.4507	0.1714	−0.2029	0.070*
C5	0.2707 (3)	0.1891 (2)	−0.2844 (2)	0.0775 (9)
H5A	0.2943	0.1704	−0.3393	0.093*
C6	0.1426 (3)	0.2159 (2)	−0.2846 (2)	0.0747 (9)
H6A	0.0796	0.2149	−0.3394	0.090*
C7	0.1079 (2)	0.24395 (17)	−0.2039 (2)	0.0633 (8)
H7A	0.0213	0.2620	−0.2039	0.076*
C8	0.2023 (2)	0.24547 (14)	−0.12211 (17)	0.0467 (5)
H8A	0.1786	0.2654	−0.0678	0.056*
O3	0.43667 (14)	0.02350 (11)	0.16182 (10)	0.0444 (4)
O4	0.28773 (16)	−0.06110 (11)	0.20372 (11)	0.0555 (4)
C9	0.3872 (2)	−0.01680 (15)	0.22212 (14)	0.0411 (5)
C10	0.4592 (2)	−0.00598 (19)	0.32311 (16)	0.0596 (7)
H10A	0.5128	−0.0550	0.3420	0.071*
H10B	0.5188	0.0414	0.3269	0.071*
C11	0.3641 (2)	0.00710 (15)	0.38924 (15)	0.0456 (5)
C12	0.3061 (3)	−0.05839 (18)	0.42846 (19)	0.0650 (7)
H12A	0.3274	−0.1128	0.4152	0.078*
C13	0.2172 (3)	−0.0439 (2)	0.4869 (2)	0.0742 (8)
H13A	0.1795	−0.0887	0.5129	0.089*
C14	0.1839 (3)	0.0353 (2)	0.50716 (18)	0.0636 (7)
H14A	0.1238	0.0447	0.5467	0.076*
C15	0.2394 (3)	0.10011 (19)	0.46888 (19)	0.0631 (7)
H15A	0.2170	0.1543	0.4821	0.076*
C16	0.3284 (3)	0.08655 (17)	0.41081 (18)	0.0563 (6)
H16A	0.3655	0.1319	0.3854	0.068*
N1	0.23495 (15)	−0.01459 (10)	−0.09298 (11)	0.0314 (3)
N2	0.19920 (15)	0.08350 (10)	0.04221 (11)	0.0325 (3)
C17	0.2643 (2)	−0.06336 (14)	−0.16069 (14)	0.0391 (5)
H17A	0.3461	−0.0906	−0.1511	0.047*
C18	0.1775 (2)	−0.07459 (15)	−0.24405 (15)	0.0466 (5)
H18A	0.2003	−0.1090	−0.2898	0.056*
C19	0.0565 (2)	−0.03411 (16)	−0.25860 (16)	0.0495 (6)
H19A	−0.0037	−0.0413	−0.3141	0.059*
C20	0.0255 (2)	0.01729 (14)	−0.18992 (15)	0.0427 (5)
H20A	−0.0553	0.0456	−0.1988	0.051*
C21	0.11684 (18)	0.02584 (12)	−0.10760 (13)	0.0312 (4)
C22	0.09470 (17)	0.07952 (12)	−0.02961 (13)	0.0306 (4)
C23	−0.02197 (19)	0.12337 (13)	−0.02906 (15)	0.0383 (5)
H23A	−0.0940	0.1183	−0.0781	0.046*
C24	−0.0295 (2)	0.17477 (14)	0.04555 (16)	0.0440 (5)
H24A	−0.1070	0.2047	0.0473	0.053*
C25	0.0786 (2)	0.18136 (14)	0.11732 (16)	0.0452 (5)
H25A	0.0763	0.2170	0.1671	0.054*
C26	0.1906 (2)	0.13390 (14)	0.11387 (15)	0.0405 (5)
H26A	0.2626	0.1371	0.1631	0.049*
O5	0.2460 (2)	−0.23227 (13)	0.20341 (15)	0.0773 (6)
H51	0.2485	−0.1839	0.2272	0.116*
H52	0.2711	−0.2215	0.1520	0.116*

	U11	U22	U33	U12	U13	U23
Cu	0.02265 (12)	0.03791 (15)	0.03088 (13)	0.00331 (9)	0.00258 (8)	−0.00214 (10)
O1	0.0285 (6)	0.0323 (7)	0.0433 (8)	0.0024 (5)	0.0051 (6)	0.0023 (6)
O2	0.0342 (8)	0.0455 (9)	0.0739 (11)	−0.0039 (7)	0.0121 (7)	0.0069 (8)
C1	0.0320 (10)	0.0356 (11)	0.0312 (10)	0.0014 (8)	0.0019 (8)	−0.0005 (8)
C2	0.0400 (11)	0.0334 (11)	0.0426 (11)	0.0032 (9)	0.0055 (9)	−0.0029 (9)
C3	0.0351 (10)	0.0321 (10)	0.0428 (11)	0.0030 (8)	0.0039 (8)	0.0058 (9)
C4	0.0551 (14)	0.0698 (18)	0.0468 (14)	0.0191 (13)	0.0007 (11)	−0.0008 (13)
C5	0.090 (2)	0.090 (2)	0.0448 (15)	0.0176 (18)	−0.0081 (14)	−0.0041 (15)
C6	0.0710 (19)	0.075 (2)	0.0636 (19)	0.0014 (16)	−0.0254 (15)	0.0121 (15)
C7	0.0376 (12)	0.0606 (17)	0.086 (2)	0.0029 (11)	−0.0042 (13)	0.0222 (15)
C8	0.0377 (11)	0.0428 (12)	0.0599 (14)	0.0023 (9)	0.0099 (10)	0.0093 (11)
O3	0.0309 (7)	0.0674 (10)	0.0337 (8)	0.0018 (7)	0.0031 (6)	−0.0036 (7)
O4	0.0500 (9)	0.0661 (11)	0.0491 (10)	−0.0099 (8)	0.0062 (7)	−0.0053 (8)
C9	0.0315 (10)	0.0574 (14)	0.0335 (11)	0.0116 (10)	0.0037 (8)	−0.0074 (10)
C10	0.0410 (12)	0.100 (2)	0.0355 (12)	0.0106 (13)	0.0012 (9)	−0.0053 (13)
C11	0.0457 (12)	0.0607 (15)	0.0286 (10)	0.0041 (11)	0.0024 (9)	0.0002 (10)
C12	0.090 (2)	0.0494 (15)	0.0579 (16)	0.0079 (14)	0.0187 (15)	0.0018 (13)
C13	0.096 (2)	0.071 (2)	0.0629 (18)	−0.0154 (18)	0.0345 (16)	0.0074 (16)
C14	0.0631 (16)	0.085 (2)	0.0467 (15)	−0.0023 (15)	0.0211 (12)	−0.0068 (15)
C15	0.0716 (18)	0.0637 (17)	0.0549 (16)	0.0097 (14)	0.0144 (13)	−0.0113 (13)
C16	0.0660 (16)	0.0532 (15)	0.0509 (14)	−0.0050 (12)	0.0140 (12)	0.0018 (12)
N1	0.0259 (7)	0.0354 (9)	0.0325 (8)	0.0004 (6)	0.0044 (6)	−0.0008 (7)
N2	0.0259 (7)	0.0372 (9)	0.0340 (8)	0.0012 (7)	0.0046 (6)	−0.0020 (7)
C17	0.0321 (10)	0.0462 (12)	0.0395 (11)	0.0043 (9)	0.0080 (8)	−0.0070 (9)
C18	0.0477 (12)	0.0546 (14)	0.0372 (11)	0.0004 (11)	0.0071 (9)	−0.0115 (10)
C19	0.0462 (13)	0.0617 (15)	0.0358 (12)	0.0001 (11)	−0.0044 (9)	−0.0055 (11)
C20	0.0333 (10)	0.0501 (13)	0.0413 (12)	0.0052 (9)	−0.0018 (9)	0.0010 (10)
C21	0.0260 (9)	0.0332 (10)	0.0341 (10)	−0.0011 (7)	0.0048 (7)	0.0023 (8)
C22	0.0256 (8)	0.0330 (10)	0.0330 (10)	−0.0009 (8)	0.0052 (7)	0.0034 (8)
C23	0.0282 (9)	0.0416 (11)	0.0440 (11)	0.0037 (8)	0.0040 (8)	0.0025 (9)
C24	0.0323 (10)	0.0449 (12)	0.0565 (14)	0.0080 (9)	0.0125 (9)	−0.0031 (10)
C25	0.0416 (11)	0.0467 (13)	0.0492 (13)	0.0034 (10)	0.0135 (10)	−0.0125 (10)
C26	0.0339 (10)	0.0462 (12)	0.0405 (11)	0.0011 (9)	0.0046 (8)	−0.0085 (10)
O5	0.0807 (14)	0.0718 (13)	0.0769 (14)	−0.0005 (11)	0.0082 (11)	0.0222 (11)

Cu—O3	1.9558 (15)	C12—H12A	0.9300
Cu—O1i	1.9808 (14)	C13—C14	1.363 (4)
Cu—N1	2.0107 (17)	C13—H13A	0.9300
Cu—N2	2.0234 (16)	C14—C15	1.356 (4)
Cu—O1	2.3668 (14)	C14—H14A	0.9300
O1—C1	1.286 (2)	C15—C16	1.372 (4)
O1—Cui	1.9808 (14)	C15—H15A	0.9300
O2—C1	1.231 (2)	C16—H16A	0.9300
C1—C2	1.518 (3)	N1—C17	1.340 (3)
C2—C3	1.517 (3)	N1—C21	1.351 (2)
C2—H2A	0.9700	N2—C26	1.340 (3)
C2—H2B	0.9700	N2—C22	1.352 (2)
C3—C4	1.381 (3)	C17—C18	1.380 (3)
C3—C8	1.389 (3)	C17—H17A	0.9300
C4—C5	1.388 (4)	C18—C19	1.377 (3)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.377 (4)	C19—C20	1.382 (3)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.371 (4)	C20—C21	1.386 (3)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.390 (3)	C21—C22	1.481 (3)
C7—H7A	0.9300	C22—C23	1.385 (3)
C8—H8A	0.9300	C23—C24	1.382 (3)
O3—C9	1.272 (3)	C23—H23A	0.9300
O4—C9	1.228 (3)	C24—C25	1.379 (3)
C9—C10	1.533 (3)	C24—H24A	0.9300
C10—C11	1.508 (3)	C25—C26	1.383 (3)
C10—H10A	0.9700	C25—H25A	0.9300
C10—H10B	0.9700	C26—H26A	0.9300
C11—C16	1.380 (3)	O5—H51	0.8494
C11—C12	1.383 (4)	O5—H52	0.8560
C12—C13	1.379 (4)
O3—Cu—O1i	90.90 (6)	C13—C12—C11	120.8 (3)
O3—Cu—N1	171.79 (6)	C13—C12—H12A	119.6
O1i—Cu—N1	95.55 (6)	C11—C12—H12A	119.6
O3—Cu—N2	92.68 (7)	C14—C13—C12	120.8 (3)
O1i—Cu—N2	174.44 (6)	C14—C13—H13A	119.6
N1—Cu—N2	80.52 (7)	C12—C13—H13A	119.6
O3—Cu—O1	89.67 (6)	C15—C14—C13	119.1 (3)
O1i—Cu—O1	77.72 (6)	C15—C14—H14A	120.5
N1—Cu—O1	96.65 (6)	C13—C14—H14A	120.5
N2—Cu—O1	106.54 (6)	C14—C15—C16	120.7 (3)
C1—O1—Cui	118.61 (12)	C14—C15—H15A	119.7
C1—O1—Cu	138.41 (12)	C16—C15—H15A	119.7
Cui—O1—Cu	102.28 (6)	C15—C16—C11	121.5 (3)
O2—C1—O1	123.49 (18)	C15—C16—H16A	119.3
O2—C1—C2	120.32 (19)	C11—C16—H16A	119.3
O1—C1—C2	116.18 (17)	C17—N1—C21	118.68 (17)
C3—C2—C1	113.63 (17)	C17—N1—Cu	126.20 (13)
C3—C2—H2A	108.8	C21—N1—Cu	115.11 (13)
C1—C2—H2A	108.8	C26—N2—C22	118.62 (16)
C3—C2—H2B	108.8	C26—N2—Cu	126.61 (13)
C1—C2—H2B	108.8	C22—N2—Cu	114.59 (13)
H2A—C2—H2B	107.7	N1—C17—C18	122.32 (19)
C4—C3—C8	118.3 (2)	N1—C17—H17A	118.8
C4—C3—C2	121.36 (19)	C18—C17—H17A	118.8
C8—C3—C2	120.3 (2)	C19—C18—C17	119.0 (2)
C3—C4—C5	120.9 (2)	C19—C18—H18A	120.5
C3—C4—H4A	119.6	C17—C18—H18A	120.5
C5—C4—H4A	119.6	C18—C19—C20	119.4 (2)
C6—C5—C4	120.1 (3)	C18—C19—H19A	120.3
C6—C5—H5A	120.0	C20—C19—H19A	120.3
C4—C5—H5A	120.0	C19—C20—C21	118.9 (2)
C7—C6—C5	120.0 (2)	C19—C20—H20A	120.6
C7—C6—H6A	120.0	C21—C20—H20A	120.6
C5—C6—H6A	120.0	N1—C21—C20	121.75 (19)
C6—C7—C8	119.9 (2)	N1—C21—C22	114.69 (16)
C6—C7—H7A	120.1	C20—C21—C22	123.56 (18)
C8—C7—H7A	120.1	N2—C22—C23	121.76 (18)
C3—C8—C7	120.9 (2)	N2—C22—C21	114.49 (16)
C3—C8—H8A	119.5	C23—C22—C21	123.75 (17)
C7—C8—H8A	119.5	C24—C23—C22	118.88 (19)
C9—O3—Cu	114.65 (14)	C24—C23—H23A	120.6
O4—C9—O3	124.2 (2)	C22—C23—H23A	120.6
O4—C9—C10	120.3 (2)	C25—C24—C23	119.50 (19)
O3—C9—C10	115.5 (2)	C25—C24—H24A	120.3
C11—C10—C9	112.61 (19)	C23—C24—H24A	120.3
C11—C10—H10A	109.1	C24—C25—C26	118.7 (2)
C9—C10—H10A	109.1	C24—C25—H25A	120.6
C11—C10—H10B	109.1	C26—C25—H25A	120.6
C9—C10—H10B	109.1	N2—C26—C25	122.46 (19)
H10A—C10—H10B	107.8	N2—C26—H26A	118.8
C16—C11—C12	117.1 (2)	C25—C26—H26A	118.8
C16—C11—C10	120.3 (2)	H51—O5—H52	100.6
C12—C11—C10	122.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.85	2.05	2.781 (3)	143
O5—H52···O2i	0.86	2.08	2.931 (3)	174
C20—H20A···O4ii	0.93	2.38	3.245 (3)	156
C24—H24A···O2iii	0.93	2.48	3.172 (3)	131
C25—H25A···O5iv	0.93	2.50	3.201 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4	0.85	2.05	2.781 (3)	143
O5—H52⋯O2i	0.86	2.08	2.931 (3)	174
C20—H20A⋯O4ii	0.93	2.38	3.245 (3)	156
C24—H24A⋯O2iii	0.93	2.48	3.172 (3)	131
C25—H25A⋯O5iv	0.93	2.50	3.201 (3)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .