(2,2'-Bipyridine-κN,N')bis-(3-meth-oxy-benzoato-κO,O)copper(II) mono-hydrate.

The title compound, [Cu(C(8)H(7)O(3))(2)(C(10)H(8)N(2))]·H(2)O, is comprised of a Cu(II) ion, two 3-meth-oxy-benzoate ligands, a 2,2'-bipyridine (bipy) ligand and one uncoordinated water mol-ecule. The Cu(II) ion and the water O atom lie on a twofold axis. The Cu(II) ion exhibits a six-coordinate distorted octa-hedral geometry, with two N atoms from the bipy ligand [Cu-N = 1.9996 (16) Å] and four O atoms from two 3-meth-oxy-benzoate ligands [Cu-O = 1.9551 (15) and 2.6016 (16) Å]. The mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For hydrogen bonds and crystal engineering, see: Aakeröy & Seddon (1993 ▶). For potential applications of transition metal complexes, see: Liu et al. (2007 ▶); Shibasaki & Yoshikawa (2002 ▶). For carboxylate compounds with six-coordinate metal atoms, see: Liu et al. (2010 ▶); Su et al. (2005 ▶).

Experimental

Crystal data

[Cu(C8H7O3)2(C10H8N2)]·H2O

M = 540.01

Monoclinic,

a = 19.888 (4) Å

b = 10.887 (2) Å

c = 11.612 (2) Å

β = 103.62 (3)°

V = 2443.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.94 mm−1

T = 293 K

0.1 × 0.1 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.710, T max = 0.780

12080 measured reflections

2796 independent reflections

2391 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.05

2796 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 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 datablocks global, I. DOI: 10.1107/S1600536811005563/rn2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005563/rn2078Isup2.hkl

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

[Cu(C8H7O3)2(C10H8N2)]·H2O	F(000) = 1116
Mr = 540.01	Dx = 1.468 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12080 reflections
a = 19.888 (4) Å	θ = 3.6–27.5°
b = 10.887 (2) Å	µ = 0.94 mm−1
c = 11.612 (2) Å	T = 293 K
β = 103.62 (3)°	Block, blue
V = 2443.5 (8) Å3	0.1 × 0.1 × 0.1 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2796 independent reflections
Radiation source: fine-focus sealed tube	2391 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.6°
ω scans	h = −25→25
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.710, Tmax = 0.78	l = −15→14
12080 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.7842P] where P = (Fo2 + 2Fc2)/3
2796 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.39 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	0.0000	0.52776 (3)	0.7500	0.04304 (15)
O1	−0.04555 (7)	0.40392 (14)	0.82712 (14)	0.0539 (4)
O2	−0.12489 (8)	0.44707 (15)	0.66421 (15)	0.0598 (4)
O3	−0.15000 (9)	0.11263 (17)	1.05759 (15)	0.0669 (5)
N1	−0.03034 (8)	0.66715 (15)	0.83787 (14)	0.0426 (4)
C1	−0.10582 (10)	0.39069 (18)	0.75900 (19)	0.0470 (5)
C2	−0.15286 (10)	0.30133 (18)	0.79947 (19)	0.0475 (5)
C3	−0.21724 (12)	0.2726 (2)	0.7265 (2)	0.0611 (6)
H3A	−0.2317	0.3089	0.6523	0.073*
C4	−0.25923 (13)	0.1895 (3)	0.7658 (3)	0.0724 (7)
H4A	−0.3021	0.1702	0.7170	0.087*
C5	−0.23949 (12)	0.1344 (2)	0.8754 (3)	0.0646 (6)
H5A	−0.2688	0.0790	0.9003	0.078*
C6	−0.17571 (11)	0.16247 (19)	0.9479 (2)	0.0534 (5)
C7	−0.13269 (10)	0.24562 (19)	0.9099 (2)	0.0498 (5)
H7A	−0.0898	0.2643	0.9590	0.060*
C8	−0.19197 (18)	0.0270 (3)	1.1014 (3)	0.0818 (9)
H8A	−0.1674	−0.0022	1.1777	0.123*
H8B	−0.2028	−0.0410	1.0476	0.123*
H8C	−0.2340	0.0664	1.1085	0.123*
C9	−0.06227 (11)	0.6578 (2)	0.92759 (18)	0.0492 (5)
H9A	−0.0705	0.5802	0.9549	0.059*
C10	−0.08304 (12)	0.7594 (2)	0.97979 (19)	0.0557 (5)
H10A	−0.1055	0.7507	1.0411	0.067*
C11	−0.07033 (13)	0.8737 (2)	0.9407 (2)	0.0599 (6)
H11A	−0.0838	0.9434	0.9757	0.072*
C12	−0.03730 (12)	0.8849 (2)	0.8490 (2)	0.0552 (5)
H12A	−0.0282	0.9619	0.8215	0.066*
C13	−0.01811 (10)	0.77943 (18)	0.79901 (17)	0.0426 (4)
O4	0.0000	0.1586 (2)	0.7500	0.0842 (8)
H41	−0.0138	0.2109	0.7975	0.126*

	U11	U22	U33	U12	U13	U23
Cu	0.0395 (2)	0.0333 (2)	0.0560 (2)	0.000	0.01071 (15)	0.000
O1	0.0423 (8)	0.0427 (8)	0.0740 (10)	−0.0074 (6)	0.0083 (7)	0.0071 (7)
O2	0.0532 (9)	0.0576 (9)	0.0692 (10)	0.0083 (7)	0.0159 (8)	0.0082 (8)
O3	0.0646 (10)	0.0641 (11)	0.0774 (11)	−0.0110 (8)	0.0277 (9)	0.0081 (8)
N1	0.0407 (9)	0.0405 (9)	0.0468 (9)	−0.0013 (7)	0.0108 (7)	0.0020 (6)
C1	0.0435 (11)	0.0356 (10)	0.0642 (12)	0.0055 (8)	0.0174 (9)	−0.0021 (9)
C2	0.0367 (10)	0.0361 (10)	0.0696 (13)	0.0015 (8)	0.0125 (9)	−0.0064 (9)
C3	0.0457 (12)	0.0546 (13)	0.0777 (15)	−0.0014 (10)	0.0040 (11)	−0.0038 (11)
C4	0.0400 (12)	0.0667 (16)	0.103 (2)	−0.0126 (11)	0.0024 (12)	−0.0111 (15)
C5	0.0459 (13)	0.0512 (13)	0.1009 (19)	−0.0111 (10)	0.0258 (12)	−0.0081 (12)
C6	0.0478 (12)	0.0425 (11)	0.0754 (14)	−0.0041 (9)	0.0254 (10)	−0.0069 (10)
C7	0.0383 (10)	0.0447 (11)	0.0671 (13)	−0.0052 (8)	0.0135 (9)	−0.0048 (9)
C8	0.093 (2)	0.0693 (19)	0.098 (2)	−0.0154 (15)	0.0526 (19)	0.0040 (14)
C9	0.0461 (11)	0.0513 (12)	0.0508 (11)	−0.0028 (9)	0.0127 (9)	0.0042 (9)
C10	0.0557 (13)	0.0657 (14)	0.0502 (11)	0.0017 (11)	0.0211 (10)	−0.0018 (10)
C11	0.0696 (15)	0.0536 (13)	0.0614 (13)	0.0079 (11)	0.0255 (11)	−0.0082 (10)
C12	0.0679 (14)	0.0386 (11)	0.0629 (13)	0.0042 (10)	0.0232 (11)	−0.0006 (9)
C13	0.0430 (10)	0.0384 (10)	0.0462 (10)	0.0013 (8)	0.0100 (8)	−0.0011 (7)
O4	0.124 (3)	0.0464 (14)	0.0887 (18)	0.000	0.0370 (17)	0.000

Cu—O1i	1.9551 (15)	C5—C6	1.381 (3)
Cu—O1	1.9551 (15)	C5—H5A	0.9300
Cu—N1i	1.9996 (16)	C6—C7	1.387 (3)
Cu—N1	1.9996 (16)	C7—H7A	0.9300
O1—C1	1.279 (3)	C8—H8A	0.9600
O2—C1	1.239 (3)	C8—H8B	0.9600
O3—C6	1.368 (3)	C8—H8C	0.9600
O3—C8	1.423 (3)	C9—C10	1.371 (3)
N1—C13	1.345 (2)	C9—H9A	0.9300
N1—C9	1.346 (3)	C10—C11	1.369 (3)
C1—C2	1.500 (3)	C10—H10A	0.9300
C2—C7	1.390 (3)	C11—C12	1.382 (3)
C2—C3	1.395 (3)	C11—H11A	0.9300
C3—C4	1.380 (4)	C12—C13	1.380 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.378 (4)	C13—C13i	1.483 (4)
C4—H4A	0.9300	O4—H41	0.8800
O1i—Cu—O1	92.80 (10)	O3—C6—C7	115.6 (2)
O1i—Cu—N1i	93.53 (7)	C5—C6—C7	119.8 (2)
O1—Cu—N1i	170.12 (6)	C6—C7—C2	120.8 (2)
O1i—Cu—N1	170.12 (6)	C6—C7—H7A	119.6
O1—Cu—N1	93.53 (7)	C2—C7—H7A	119.6
N1i—Cu—N1	81.25 (9)	O3—C8—H8A	109.5
C1—O1—Cu	105.20 (13)	O3—C8—H8B	109.5
C6—O3—C8	118.1 (2)	H8A—C8—H8B	109.5
C13—N1—C9	118.97 (17)	O3—C8—H8C	109.5
C13—N1—Cu	114.74 (12)	H8A—C8—H8C	109.5
C9—N1—Cu	126.27 (14)	H8B—C8—H8C	109.5
O2—C1—O1	122.66 (19)	N1—C9—C10	121.83 (19)
O2—C1—C2	121.1 (2)	N1—C9—H9A	119.1
O1—C1—C2	116.23 (18)	C10—C9—H9A	119.1
C7—C2—C3	119.2 (2)	C11—C10—C9	119.26 (19)
C7—C2—C1	120.43 (19)	C11—C10—H10A	120.4
C3—C2—C1	120.4 (2)	C9—C10—H10A	120.4
C4—C3—C2	119.1 (2)	C10—C11—C12	119.6 (2)
C4—C3—H3A	120.4	C10—C11—H11A	120.2
C2—C3—H3A	120.4	C12—C11—H11A	120.2
C5—C4—C3	121.9 (2)	C13—C12—C11	118.6 (2)
C5—C4—H4A	119.1	C13—C12—H12A	120.7
C3—C4—H4A	119.1	C11—C12—H12A	120.7
C4—C5—C6	119.2 (2)	N1—C13—C12	121.68 (17)
C4—C5—H5A	120.4	N1—C13—C13i	114.60 (10)
C6—C5—H5A	120.4	C12—C13—C13i	123.71 (12)
O3—C6—C5	124.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O1	0.88	2.24	3.023 (3)	147
C12—H12A···O4ii	0.93	2.41	3.339 (3)	178
C11—H11A···O3ii	0.93	2.57	3.483 (3)	166
C10—H10A···O2iii	0.93	2.66	3.342 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O1	0.88	2.24	3.023 (3)	147
C12—H12A⋯O4ii	0.93	2.41	3.339 (3)	178
C11—H11A⋯O3ii	0.93	2.57	3.483 (3)	166
C10—H10A⋯O2iii	0.93	2.66	3.342 (3)	131

Symmetry codes: (ii) ; (iii) .