Di-μ-glutarato-κO:O-bis-[aqua-(1,10-phenanthroline-κN,N')copper(II)].

In the centrosymmetric dinuclear title complex, [Cu(2)(C(5)H(6)O(4))(2)(C(12)H(18)N(2))(2)(H(2)O)(2)], the Cu(II) atom displays a dis-torted square-pyramidal coordination environment with the basal plane occupied by two phenanthroline N atoms and two O atoms from different glutarate dianions while a water mol-ecule is located at the apical position. Of the two water H atoms, one is engaged in an intra-molecular hydrogen bond with a free oxygen of the dianion whereas the second is engaged in an inter-molecular hydrogen bond, building a corrugated layer parallel to (100). These layers are further connected through π-π stacking inter-actions involving symmetry-related phenanthroline rings [centroid-centroid distance = 3.5599 (17) and 3.5617 (18) Å], building a three dimensionnal network. C-H⋯π inter-actions involving the phenanthroline ring system are also observed.

Related literature

For coordination modes of the glutarate anion, see: Ghosh et al. (2007 ▶); Kim et al. (2005 ▶); Rather & Zaworotko (2003 ▶); Zheng et al. (2004 ▶); Vaidhyanathan et al. (2004 ▶); Girginova et al. (2007 ▶).

Experimental

Crystal data

[Cu2(C5H6O4)2(C12H18N2)2(H2O)2]

M = 783.72

Monoclinic,

a = 10.2767 (11) Å

b = 10.5935 (14) Å

c = 15.5998 (16) Å

β = 107.114 (1)°

V = 1623.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.38 mm−1

T = 298 K

0.26 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.716, T max = 0.742

7937 measured reflections

2867 independent reflections

2275 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.07

2867 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811007938/dn2661sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007938/dn2661Isup2.hkl

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

[Cu2(C5H6O4)2(C12H18N2)2(H2O)2]	F(000) = 804
Mr = 783.72	Dx = 1.604 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3334 reflections
a = 10.2767 (11) Å	θ = 2.4–27.3°
b = 10.5935 (14) Å	µ = 1.38 mm−1
c = 15.5998 (16) Å	T = 298 K
β = 107.114 (1)°	Block, blue
V = 1623.1 (3) Å3	0.26 × 0.25 × 0.23 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2867 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→12
Tmin = 0.716, Tmax = 0.742	k = −12→10
7937 measured reflections	l = −18→16

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) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0346P)2 + 1.103P] where P = (Fo2 + 2Fc2)/3
2867 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 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
Cu1	0.34382 (3)	0.54797 (3)	0.21857 (2)	0.03292 (13)
N1	0.2087 (2)	0.4429 (2)	0.12652 (14)	0.0299 (5)
N2	0.3977 (2)	0.6012 (2)	0.10928 (14)	0.0318 (5)
O1	0.5068 (2)	0.61750 (19)	0.30440 (12)	0.0416 (5)
O2	0.5850 (2)	0.43066 (19)	0.28151 (13)	0.0432 (5)
O3	0.2798 (2)	0.4813 (2)	0.31524 (13)	0.0467 (5)
O4	0.1462 (3)	0.6404 (2)	0.32731 (17)	0.0689 (7)
O5	0.2215 (2)	0.74242 (19)	0.19357 (13)	0.0441 (5)
H51	0.1900	0.7287	0.2401	0.066*
H52	0.2746	0.8093	0.2014	0.066*
C1	0.5979 (3)	0.5330 (3)	0.32214 (17)	0.0318 (6)
C2	0.7228 (3)	0.5601 (3)	0.39982 (18)	0.0397 (7)
H2A	0.7284	0.6499	0.4125	0.048*
H2B	0.8038	0.5354	0.3841	0.048*
C3	0.7158 (3)	0.4873 (3)	0.48313 (18)	0.0380 (7)
H3A	0.6265	0.4993	0.4910	0.046*
H3B	0.7266	0.3980	0.4735	0.046*
C4	0.1767 (3)	0.4723 (3)	0.43155 (18)	0.0401 (7)
H4A	0.1805	0.3816	0.4242	0.048*
H4B	0.0869	0.4938	0.4356	0.048*
C5	0.2012 (3)	0.5385 (3)	0.35137 (18)	0.0387 (7)
C6	0.1142 (3)	0.3640 (3)	0.13755 (19)	0.0370 (7)
H6	0.1091	0.3496	0.1953	0.044*
C7	0.0230 (3)	0.3025 (3)	0.0664 (2)	0.0417 (7)
H7	−0.0423	0.2487	0.0768	0.050*
C8	0.0291 (3)	0.3208 (3)	−0.0187 (2)	0.0401 (7)
H8	−0.0321	0.2800	−0.0667	0.048*
C9	0.1287 (3)	0.4017 (3)	−0.03337 (18)	0.0339 (6)
C10	0.2164 (3)	0.4611 (2)	0.04186 (17)	0.0292 (6)
C11	0.3172 (3)	0.5485 (2)	0.03226 (17)	0.0294 (6)
C12	0.3286 (3)	0.5760 (3)	−0.05311 (18)	0.0368 (7)
C13	0.4278 (3)	0.6647 (3)	−0.0576 (2)	0.0445 (8)
H13	0.4398	0.6864	−0.1126	0.053*
C14	0.5061 (3)	0.7183 (3)	0.0194 (2)	0.0472 (8)
H14	0.5717	0.7776	0.0171	0.057*
C15	0.4890 (3)	0.6853 (3)	0.1024 (2)	0.0397 (7)
H15	0.5435	0.7237	0.1542	0.048*
C16	0.1444 (3)	0.4307 (3)	−0.11997 (19)	0.0429 (8)
H16	0.0881	0.3915	−0.1707	0.051*
C17	0.2384 (3)	0.5131 (3)	−0.12896 (19)	0.0453 (8)
H17	0.2455	0.5299	−0.1859	0.054*

	U11	U22	U33	U12	U13	U23
Cu1	0.0360 (2)	0.0377 (2)	0.02556 (18)	0.00182 (16)	0.00982 (14)	−0.00183 (15)
N1	0.0338 (12)	0.0290 (12)	0.0281 (11)	0.0019 (10)	0.0112 (10)	0.0016 (9)
N2	0.0340 (13)	0.0280 (12)	0.0336 (12)	0.0029 (10)	0.0105 (10)	0.0010 (10)
O1	0.0444 (12)	0.0396 (12)	0.0349 (11)	0.0059 (10)	0.0024 (9)	−0.0066 (9)
O2	0.0467 (13)	0.0412 (12)	0.0381 (11)	0.0073 (10)	0.0072 (9)	−0.0055 (9)
O3	0.0591 (14)	0.0546 (14)	0.0325 (11)	0.0083 (11)	0.0230 (10)	0.0053 (10)
O4	0.095 (2)	0.0595 (16)	0.0710 (16)	0.0257 (15)	0.0535 (15)	0.0232 (14)
O5	0.0495 (12)	0.0443 (12)	0.0379 (11)	−0.0074 (10)	0.0120 (9)	−0.0047 (9)
C1	0.0351 (15)	0.0379 (17)	0.0232 (13)	−0.0013 (13)	0.0097 (11)	0.0041 (12)
C2	0.0365 (16)	0.0490 (18)	0.0310 (14)	−0.0073 (14)	0.0057 (12)	0.0045 (13)
C3	0.0428 (17)	0.0383 (17)	0.0316 (15)	−0.0051 (13)	0.0090 (13)	0.0043 (13)
C4	0.0410 (17)	0.0481 (19)	0.0319 (15)	−0.0069 (14)	0.0117 (13)	−0.0004 (13)
C5	0.0417 (17)	0.0492 (19)	0.0253 (14)	−0.0065 (15)	0.0100 (12)	−0.0020 (14)
C6	0.0390 (16)	0.0338 (16)	0.0417 (16)	0.0031 (13)	0.0174 (13)	0.0044 (13)
C7	0.0359 (16)	0.0317 (16)	0.0580 (19)	−0.0016 (13)	0.0147 (14)	−0.0013 (14)
C8	0.0325 (16)	0.0339 (16)	0.0475 (18)	0.0027 (13)	0.0019 (13)	−0.0101 (14)
C9	0.0342 (15)	0.0326 (15)	0.0313 (14)	0.0095 (12)	0.0041 (12)	−0.0017 (12)
C10	0.0319 (14)	0.0280 (14)	0.0274 (13)	0.0071 (12)	0.0084 (11)	0.0002 (11)
C11	0.0320 (14)	0.0287 (14)	0.0287 (14)	0.0089 (12)	0.0105 (11)	0.0026 (11)
C12	0.0443 (17)	0.0357 (16)	0.0342 (15)	0.0159 (13)	0.0177 (13)	0.0100 (12)
C13	0.0488 (19)	0.0447 (19)	0.0476 (18)	0.0138 (15)	0.0260 (15)	0.0163 (15)
C14	0.0453 (18)	0.0354 (17)	0.070 (2)	0.0027 (14)	0.0307 (17)	0.0137 (16)
C15	0.0370 (16)	0.0318 (16)	0.0503 (18)	0.0004 (13)	0.0131 (14)	−0.0021 (14)
C16	0.0475 (18)	0.0480 (19)	0.0289 (15)	0.0103 (15)	0.0046 (13)	−0.0058 (13)
C17	0.058 (2)	0.055 (2)	0.0246 (15)	0.0181 (17)	0.0136 (14)	0.0054 (14)

Cu1—O3	1.947 (2)	C4—C3i	1.520 (4)
Cu1—O1	1.9545 (19)	C4—H4A	0.9700
Cu1—N1	2.014 (2)	C4—H4B	0.9700
Cu1—N2	2.022 (2)	C6—C7	1.387 (4)
Cu1—O5	2.385 (2)	C6—H6	0.9300
N1—C6	1.329 (3)	C7—C8	1.362 (4)
N1—C10	1.360 (3)	C7—H7	0.9300
N2—C15	1.320 (4)	C8—C9	1.404 (4)
N2—C11	1.362 (3)	C8—H8	0.9300
O1—C1	1.266 (3)	C9—C10	1.401 (4)
O2—C1	1.243 (3)	C9—C16	1.440 (4)
O3—C5	1.267 (3)	C10—C11	1.429 (4)
O4—C5	1.225 (4)	C11—C12	1.402 (4)
O5—H51	0.8897	C12—C13	1.403 (4)
O5—H52	0.8804	C12—C17	1.435 (4)
C1—C2	1.511 (4)	C13—C14	1.359 (4)
C2—C3	1.531 (4)	C13—H13	0.9300
C2—H2A	0.9700	C14—C15	1.401 (4)
C2—H2B	0.9700	C14—H14	0.9300
C3—C4i	1.520 (4)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.340 (5)
C3—H3B	0.9700	C16—H16	0.9300
C4—C5	1.518 (4)	C17—H17	0.9300
O3—Cu1—O1	91.32 (9)	H4A—C4—H4B	108.2
O3—Cu1—N1	91.85 (9)	O4—C5—O3	125.6 (3)
O1—Cu1—N1	165.65 (9)	O4—C5—C4	119.0 (3)
O3—Cu1—N2	173.39 (9)	O3—C5—C4	115.3 (3)
O1—Cu1—N2	94.62 (9)	N1—C6—C7	122.6 (3)
N1—Cu1—N2	81.69 (9)	N1—C6—H6	118.7
O3—Cu1—O5	99.10 (8)	C7—C6—H6	118.7
O1—Cu1—O5	95.20 (7)	C8—C7—C6	120.0 (3)
N1—Cu1—O5	98.12 (8)	C8—C7—H7	120.0
N2—Cu1—O5	83.28 (8)	C6—C7—H7	120.0
C6—N1—C10	117.9 (2)	C7—C8—C9	119.4 (3)
C6—N1—Cu1	129.16 (18)	C7—C8—H8	120.3
C10—N1—Cu1	112.87 (17)	C9—C8—H8	120.3
C15—N2—C11	117.8 (2)	C10—C9—C8	117.3 (3)
C15—N2—Cu1	129.3 (2)	C10—C9—C16	117.9 (3)
C11—N2—Cu1	112.56 (17)	C8—C9—C16	124.8 (3)
C1—O1—Cu1	108.23 (17)	N1—C10—C9	122.8 (2)
C5—O3—Cu1	125.2 (2)	N1—C10—C11	116.4 (2)
Cu1—O5—H51	91.5	C9—C10—C11	120.7 (2)
Cu1—O5—H52	113.4	N2—C11—C12	123.6 (3)
H51—O5—H52	112.2	N2—C11—C10	116.3 (2)
O2—C1—O1	123.0 (2)	C12—C11—C10	120.0 (2)
O2—C1—C2	120.8 (3)	C11—C12—C13	116.9 (3)
O1—C1—C2	116.1 (3)	C11—C12—C17	118.2 (3)
C1—C2—C3	110.1 (2)	C13—C12—C17	124.9 (3)
C1—C2—H2A	109.6	C14—C13—C12	119.0 (3)
C3—C2—H2A	109.6	C14—C13—H13	120.5
C1—C2—H2B	109.6	C12—C13—H13	120.5
C3—C2—H2B	109.6	C13—C14—C15	120.7 (3)
H2A—C2—H2B	108.1	C13—C14—H14	119.6
C4i—C3—C2	113.5 (2)	C15—C14—H14	119.6
C4i—C3—H3A	108.9	N2—C15—C14	121.9 (3)
C2—C3—H3A	108.9	N2—C15—H15	119.1
C4i—C3—H3B	108.9	C14—C15—H15	119.1
C2—C3—H3B	108.9	C17—C16—C9	121.4 (3)
H3A—C3—H3B	107.7	C17—C16—H16	119.3
C5—C4—C3i	109.7 (2)	C9—C16—H16	119.3
C5—C4—H4A	109.7	C16—C17—C12	121.8 (3)
C3i—C4—H4A	109.7	C16—C17—H17	119.1
C5—C4—H4B	109.7	C12—C17—H17	119.1
C3i—C4—H4B	109.7

Cg1 is the centroid of the N1,C6–C10 ring

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.89	1.81	2.659 (3)	158
O5—H52···O2ii	0.88	1.89	2.762 (3)	169
C2—H2A···Cg1ii	0.97	2.88	3.754 (3)	151

CgI	CgJ	centroid-to-centroid	interplanar vector	Slippage
Cg1	Cg1ii	3.5599 (17)	3.342	1.226
Cg2	Cg2iii	3.5617 (18)	3.374	1.142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C6–C10 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4	0.89	1.81	2.659 (3)	158
O5—H52⋯O2i	0.88	1.89	2.762 (3)	169
C2—H2A⋯Cg1i	0.97	2.88	3.754 (3)	151

Symmetry code: (i) .