μ-Succinato-bis­[aqua­(2,2′:6′,2′′-terpyridine)copper(II)] dinitrate dihydrate

Mei, C.; Lei, Q.; Zhang, P.

doi:10.1107/S1600536810006811

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages m346-m347

doi:10.1107/S1600536810006811

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μ-Succinato-bis[aqua(2,2′:6′,2′′-terpyridine)copper(II)] dinitrate dihydrate

Chongzhen Mei,^a ^* Qingduo Lei ^a and Peng Zhang ^a

^aInstitute of Environmental and Municipal Engineering, North China University of Water Conservancy and Electric Power, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: meichongzhen@163.com

(Received 4 February 2010; accepted 23 February 2010; online 27 February 2010)

The title compound, [Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂·2H₂O, was synthesized under hydrothermal conditions. The dinuclear copper complex is located on a crystallographic inversion centre. The Cu^II ion is pentacoordinated in a tetragonal–pyramidal geometry, with one O atom of a succinate dianion and three N atoms of a 2,2′:6′,2′′-terpyridine ligand occupying the basal plane, and a water O atom located at the apical site. In the crystal structure, O—H⋯O hydrogen bonding links the molecules into a chain parallel to the a axis.

Related literature

For background to the use of saturated aliphatic carboxylate ligands in the preparation of metal-organic complexes, see: Brusau et al. (2000 ); Rastsvetaeva et al. (1996 ). For related structures, see: Li et al. (2009 ); Ke et al. (2009 ); Jin et al. (2008 ); He & Huang (2008 ); He et al. (2007 ); Duangthongyou & Siripaisarnpipat (2008 ); Liu (2009 ); Ng (1998 ).

Experimental

Crystal data

[Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂·2H₂O
M_r = 905.77
Triclinic, $[P \overline 1]$
a = 7.397 (4) Å
b = 10.650 (5) Å
c = 12.574 (6) Å
α = 70.196 (9)°
β = 83.512 (9)°
γ = 83.836 (10)°
V = 923.5 (8) Å³
Z = 1
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 296 K
0.34 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.679, T_max = 0.724
4998 measured reflections
3211 independent reflections
2951 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.137
S = 0.98
3211 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.917 (2)
Cu1—N3	1.937 (3)
Cu1—N4	2.038 (3)
Cu1—N2	2.049 (3)
Cu1—O1W	2.260 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2WB⋯O1ⁱ	0.85	2.33	3.101 (4)	150
O2W—H2WA⋯O3ⁱⁱ	0.85	2.32	3.138 (7)	162
O1W—H1WB⋯O2W	0.85	1.98	2.831 (4)	174
O1W—H1WA⋯O2ⁱⁱⁱ	0.85	1.92	2.755 (3)	167
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006811/kj2141sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006811/kj2141Isup2.hkl

checkCIF report

Comment top

As an important family of multidentate O-donor ligands, saturated aliphatic carboxylate ligands have been extensively employed in the preparation of metal-organic complexes (Duangthongyou & Siripaisarnpipat, 2008; He & Huang, 2008; Jin et al., 2008; Li et al., 2009; Liu, 2009; Ke et al., 2009). The succinate dianion has been used as a bridging ligand in the preparation of multinuclear metal complexes. A variety of bridging modes have been found (Ng,1998; Rastsvetaeva et al., 1996; Brusau et al., 2000; He et al., 2007). We report herein the synthesis and crystal stucture of a new succinate complex [Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂.2H₂O.

In the centrosymmetric dinuclear copper complex (Fig. 1) each of the Cu^II ions is pentacoordinated, with one O atom of a succinate dianion and three N atoms of a 2,2':6',2''-terpyridine ligand occupying the basal plane, and a water O atom completing the square-pyramidal geometry from the apical site (Fig. 1). The atoms N2, N3, N4 and O1 are nearly coplanar, with the maximum deviation from the least-squares plane of 0.0292 (13) Å. The Cu atom is displaced by 0.1281 (11) Å from this plane towards the apical O atom.

With O—H···O hydrogen bonds between the coordinated water molecule and the carboxylate group, (Table 1), a one-dimensional chain running parallel to the a axis is formed as shown in Fig.2. The uncoordinated water provides an extra link and thereby strengthens the chain and also forms a link to the nitrate counterions.

Related literature top

For background to the use of saturated aliphatic carboxylate ligands in the preparation of metal-organic complexes, see: Brusau et al. (2000); Rastsvetaeva et al. (1996). For related structures, see: Li et al. (2009); Ke et al. (2009); Jin et al. (2008); He & Huang (2008); He et al. (2007); Duangthongyou & Siripaisarnpipat, 2008; Liu (2009); Ng (1998).

Experimental top

The title complound was synthesized hydrothermally in a teflon-lined autoclave (25 ml) by heating a mixture of succinic acid (0.2 mmol), 2,2':6',2''-terpyridine (0.4 mmol), Cu(NO₃)₂.4H₂O (0.2 mmol) and Et₃N (1 ml) in water (10 ml) at 393 K for 3 days. The autoclave was slowly cooled to room temperature. Crystals suitable for X-ray analysis were obtained directly from the reaction product.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title complound. Hydrogen-bond interactions are drawn with dashed lines.

µ-Succinato-bis[aqua(2,2':6',2''-terpyridine)copper(II)] dinitrate dihydrate top

Crystal data top

[Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂·2H₂O	Z = 1
M_r = 905.77	F(000) = 464
Triclinic, P1	D_x = 1.629 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.397 (4) Å	Cell parameters from 4421 reflections
b = 10.650 (5) Å	θ = 3.3–28.0°
c = 12.574 (6) Å	µ = 1.23 mm⁻¹
α = 70.196 (9)°	T = 296 K
β = 83.512 (9)°	Block, colourless
γ = 83.836 (10)°	0.34 × 0.32 × 0.28 mm
V = 923.5 (8) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	2951 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.679, T_max = 0.724	k = −12→11
4998 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.1057P)² + 0.320P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3211 reflections	Δρ_max = 0.70 e Å⁻³
263 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), F_c^*=kF_c[1+0.001xF_c²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (7)

Crystal data top

[Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂·2H₂O	γ = 83.836 (10)°
M_r = 905.77	V = 923.5 (8) Å³
Triclinic, P1	Z = 1
a = 7.397 (4) Å	Mo Kα radiation
b = 10.650 (5) Å	µ = 1.23 mm⁻¹
c = 12.574 (6) Å	T = 296 K
α = 70.196 (9)°	0.34 × 0.32 × 0.28 mm
β = 83.512 (9)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2951 reflections with I > 2σ(I)
T_min = 0.679, T_max = 0.724	R_int = 0.096
4998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 0.98	Δρ_max = 0.70 e Å⁻³
3211 reflections	Δρ_min = −0.67 e Å⁻³
263 parameters

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.24585 (4)	0.64732 (3)	0.22948 (2)	0.0286 (2)
O1W	0.5317 (3)	0.5692 (3)	0.1875 (2)	0.0493 (6)
H1WA	0.6382	0.5971	0.1717	0.059*
H1WB	0.5296	0.5065	0.1603	0.059*
N2	0.2116 (3)	0.4762 (3)	0.3654 (2)	0.0341 (6)
N3	0.2929 (3)	0.7096 (3)	0.3510 (2)	0.0334 (6)
N4	0.2612 (4)	0.8463 (3)	0.1423 (2)	0.0356 (6)
C1	0.1650 (5)	0.3580 (4)	0.3636 (3)	0.0448 (8)
H1	0.1450	0.3499	0.2946	0.054*
C2	0.1462 (5)	0.2482 (4)	0.4615 (4)	0.0540 (9)
H2	0.1150	0.1674	0.4581	0.065*
C3	0.1743 (5)	0.2605 (4)	0.5637 (3)	0.0573 (10)
H3	0.1612	0.1882	0.6304	0.069*
C4	0.2222 (5)	0.3814 (4)	0.5667 (3)	0.0501 (9)
H4	0.2422	0.3914	0.6351	0.060*
C5	0.2399 (4)	0.4875 (3)	0.4657 (3)	0.0371 (7)
C6	0.2890 (4)	0.6223 (3)	0.4581 (3)	0.0360 (7)
C7	0.3259 (5)	0.6642 (4)	0.5456 (3)	0.0495 (9)
H7	0.3256	0.6049	0.6195	0.059*
C8	0.3633 (5)	0.7967 (5)	0.5210 (3)	0.0558 (10)
H8	0.3883	0.8260	0.5793	0.067*
C9	0.3642 (5)	0.8862 (4)	0.4107 (4)	0.0516 (9)
H9	0.3898	0.9747	0.3942	0.062*
C10	0.3253 (4)	0.8388 (3)	0.3258 (3)	0.0381 (7)
C11	0.3088 (4)	0.9175 (3)	0.2045 (3)	0.0378 (7)
C12	0.3356 (5)	1.0526 (3)	0.1567 (3)	0.0509 (9)
H12	0.3709	1.0998	0.2001	0.061*
C13	0.3088 (5)	1.1167 (4)	0.0423 (4)	0.0569 (10)
H13	0.3267	1.2072	0.0083	0.068*
C14	0.2558 (5)	1.0446 (4)	−0.0195 (3)	0.0526 (9)
H14	0.2342	1.0863	−0.0953	0.063*
C15	0.2352 (5)	0.9106 (3)	0.0317 (3)	0.0427 (8)
H15	0.2020	0.8621	−0.0113	0.051*
O1	0.1725 (3)	0.5935 (2)	0.11084 (18)	0.0346 (5)
O2	−0.1129 (3)	0.6332 (2)	0.17197 (19)	0.0418 (5)
C16	−0.0007 (4)	0.5965 (3)	0.1065 (2)	0.0288 (6)
C17	−0.0602 (4)	0.5554 (3)	0.0128 (3)	0.0388 (7)
H17A	−0.1834	0.5272	0.0337	0.047*
H17B	−0.0632	0.6329	−0.0556	0.047*
N1	0.1320 (5)	0.8852 (4)	0.7310 (3)	0.0583 (9)
O3	0.2712 (7)	0.9214 (6)	0.7484 (4)	0.1279 (18)
O4	0.0270 (5)	0.9562 (4)	0.6617 (3)	0.0940 (12)
O5	0.1130 (8)	0.7657 (4)	0.7705 (4)	0.1219 (17)
O2W	0.5518 (4)	0.3538 (3)	0.1018 (3)	0.0623 (7)
H2WA	0.6184	0.2825	0.1302	0.075*
H2WB	0.6029	0.3963	0.0374	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0298 (3)	0.0333 (3)	0.0296 (3)	0.00097 (16)	−0.00715 (15)	−0.01870 (17)
O1W	0.0279 (11)	0.0587 (15)	0.0753 (16)	0.0008 (10)	0.0012 (11)	−0.0434 (13)
N2	0.0310 (13)	0.0389 (13)	0.0353 (13)	0.0019 (11)	−0.0049 (10)	−0.0166 (11)
N3	0.0310 (13)	0.0439 (14)	0.0343 (12)	0.0067 (11)	−0.0098 (10)	−0.0255 (11)
N4	0.0366 (14)	0.0353 (13)	0.0397 (13)	0.0043 (11)	−0.0072 (11)	−0.0193 (11)
C1	0.0395 (17)	0.0459 (18)	0.0524 (19)	−0.0009 (15)	−0.0061 (14)	−0.0205 (15)
C2	0.0411 (19)	0.0442 (19)	0.071 (2)	−0.0029 (16)	−0.0040 (17)	−0.0116 (17)
C3	0.0428 (19)	0.059 (2)	0.053 (2)	0.0043 (17)	0.0019 (16)	−0.0007 (17)
C4	0.0449 (19)	0.065 (2)	0.0345 (16)	0.0085 (17)	−0.0017 (14)	−0.0136 (16)
C5	0.0278 (15)	0.0488 (18)	0.0330 (14)	0.0087 (13)	−0.0025 (11)	−0.0149 (13)
C6	0.0273 (15)	0.0522 (18)	0.0340 (15)	0.0081 (13)	−0.0058 (11)	−0.0233 (13)
C7	0.0391 (18)	0.080 (3)	0.0383 (17)	0.0101 (18)	−0.0097 (14)	−0.0334 (17)
C8	0.046 (2)	0.084 (3)	0.060 (2)	0.0086 (19)	−0.0143 (17)	−0.054 (2)
C9	0.0449 (19)	0.060 (2)	0.069 (2)	0.0026 (17)	−0.0116 (17)	−0.0462 (19)
C10	0.0298 (15)	0.0463 (18)	0.0511 (18)	0.0047 (13)	−0.0087 (13)	−0.0334 (15)
C11	0.0284 (15)	0.0378 (16)	0.0547 (19)	0.0052 (12)	−0.0076 (13)	−0.0262 (14)
C12	0.047 (2)	0.0402 (18)	0.075 (3)	0.0030 (16)	−0.0072 (18)	−0.0330 (18)
C13	0.050 (2)	0.0347 (18)	0.080 (3)	0.0070 (16)	−0.0016 (19)	−0.0162 (18)
C14	0.045 (2)	0.050 (2)	0.054 (2)	0.0114 (17)	−0.0087 (16)	−0.0086 (16)
C15	0.0404 (17)	0.0430 (18)	0.0440 (17)	0.0064 (14)	−0.0092 (14)	−0.0145 (14)
O1	0.0289 (11)	0.0497 (13)	0.0371 (11)	0.0008 (9)	−0.0093 (8)	−0.0286 (10)
O2	0.0328 (11)	0.0611 (14)	0.0450 (12)	0.0029 (10)	−0.0050 (9)	−0.0364 (11)
C16	0.0299 (14)	0.0288 (13)	0.0329 (14)	0.0023 (11)	−0.0079 (11)	−0.0165 (11)
C17	0.0298 (15)	0.0524 (19)	0.0490 (17)	0.0093 (14)	−0.0127 (13)	−0.0368 (15)
N1	0.063 (2)	0.059 (2)	0.0496 (17)	0.0021 (17)	0.0010 (16)	−0.0169 (15)
O3	0.120 (4)	0.167 (5)	0.118 (3)	−0.050 (3)	−0.041 (3)	−0.054 (3)
O4	0.083 (3)	0.089 (3)	0.100 (3)	0.016 (2)	−0.025 (2)	−0.020 (2)
O5	0.164 (5)	0.074 (3)	0.105 (3)	−0.018 (3)	−0.020 (3)	0.005 (2)
O2W	0.0656 (17)	0.0518 (15)	0.0742 (18)	0.0006 (13)	−0.0035 (14)	−0.0290 (14)

Geometric parameters (Å, º) top

Cu1—O1	1.917 (2)	C8—C9	1.391 (6)
Cu1—N3	1.937 (3)	C8—H8	0.9300
Cu1—N4	2.038 (3)	C9—C10	1.394 (5)
Cu1—N2	2.049 (3)	C9—H9	0.9300
Cu1—O1W	2.260 (2)	C10—C11	1.483 (5)
O1W—H1WA	0.8501	C11—C12	1.385 (5)
O1W—H1WB	0.8501	C12—C13	1.394 (6)
N2—C5	1.348 (4)	C12—H12	0.9300
N2—C1	1.349 (5)	C13—C14	1.372 (6)
N3—C10	1.345 (4)	C13—H13	0.9300
N3—C6	1.351 (4)	C14—C15	1.370 (5)
N4—C15	1.351 (4)	C14—H14	0.9300
N4—C11	1.354 (4)	C15—H15	0.9300
C1—C2	1.387 (5)	O1—C16	1.285 (4)
C1—H1	0.9300	O2—C16	1.230 (3)
C2—C3	1.376 (6)	C16—C17	1.510 (4)
C2—H2	0.9300	C17—C17ⁱ	1.503 (6)
C3—C4	1.386 (6)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.389 (5)	N1—O3	1.204 (6)
C4—H4	0.9300	N1—O5	1.217 (5)
C5—C6	1.487 (5)	N1—O4	1.231 (5)
C6—C7	1.383 (5)	O2W—H2WA	0.8499
C7—C8	1.390 (6)	O2W—H2WB	0.8500
C7—H7	0.9300

O1—Cu1—N3	173.78 (9)	C6—C7—H7	120.6
O1—Cu1—N4	98.53 (10)	C8—C7—H7	120.6
N3—Cu1—N4	80.04 (11)	C7—C8—C9	121.1 (3)
O1—Cu1—N2	100.55 (11)	C7—C8—H8	119.5
N3—Cu1—N2	79.94 (12)	C9—C8—H8	119.5
N4—Cu1—N2	158.56 (11)	C8—C9—C10	117.8 (4)
O1—Cu1—O1W	86.91 (9)	C8—C9—H9	121.1
N3—Cu1—O1W	99.30 (10)	C10—C9—H9	121.1
N4—Cu1—O1W	100.14 (10)	N3—C10—C9	120.2 (3)
N2—Cu1—O1W	90.58 (10)	N3—C10—C11	112.8 (3)
Cu1—O1W—H1WA	138.1	C9—C10—C11	127.0 (3)
Cu1—O1W—H1WB	111.0	N4—C11—C12	121.6 (3)
H1WA—O1W—H1WB	107.7	N4—C11—C10	114.1 (3)
C5—N2—C1	118.7 (3)	C12—C11—C10	124.3 (3)
C5—N2—Cu1	114.3 (2)	C11—C12—C13	118.9 (3)
C1—N2—Cu1	127.0 (2)	C11—C12—H12	120.6
C10—N3—C6	122.5 (3)	C13—C12—H12	120.6
C10—N3—Cu1	118.7 (2)	C14—C13—C12	119.2 (3)
C6—N3—Cu1	118.8 (2)	C14—C13—H13	120.4
C15—N4—C11	118.5 (3)	C12—C13—H13	120.4
C15—N4—Cu1	127.4 (2)	C15—C14—C13	119.3 (4)
C11—N4—Cu1	114.1 (2)	C15—C14—H14	120.3
N2—C1—C2	122.0 (3)	C13—C14—H14	120.3
N2—C1—H1	119.0	N4—C15—C14	122.4 (3)
C2—C1—H1	119.0	N4—C15—H15	118.8
C3—C2—C1	119.0 (4)	C14—C15—H15	118.8
C3—C2—H2	120.5	C16—O1—Cu1	115.18 (17)
C1—C2—H2	120.5	O2—C16—O1	123.0 (3)
C2—C3—C4	119.5 (3)	O2—C16—C17	121.3 (3)
C2—C3—H3	120.2	O1—C16—C17	115.7 (2)
C4—C3—H3	120.2	C17ⁱ—C17—C16	114.3 (3)
C3—C4—C5	118.7 (4)	C17ⁱ—C17—H17A	108.7
C3—C4—H4	120.6	C16—C17—H17A	108.7
C5—C4—H4	120.6	C17ⁱ—C17—H17B	108.7
N2—C5—C4	122.0 (3)	C16—C17—H17B	108.7
N2—C5—C6	114.2 (3)	H17A—C17—H17B	107.6
C4—C5—C6	123.8 (3)	O3—N1—O5	116.3 (5)
N3—C6—C7	119.7 (3)	O3—N1—O4	123.9 (5)
N3—C6—C5	112.7 (3)	O5—N1—O4	118.6 (5)
C7—C6—C5	127.6 (3)	H2WA—O2W—H2WB	107.7
C6—C7—C8	118.7 (3)

O1—Cu1—N2—C5	−174.99 (19)	N2—C5—C6—N3	1.1 (4)
N3—Cu1—N2—C5	−1.29 (19)	C4—C5—C6—N3	−178.3 (3)
N4—Cu1—N2—C5	−22.4 (4)	N2—C5—C6—C7	180.0 (3)
O1W—Cu1—N2—C5	98.0 (2)	C4—C5—C6—C7	0.6 (5)
O1—Cu1—N2—C1	5.0 (3)	N3—C6—C7—C8	1.0 (5)
N3—Cu1—N2—C1	178.7 (3)	C5—C6—C7—C8	−177.8 (3)
N4—Cu1—N2—C1	157.6 (3)	C6—C7—C8—C9	0.0 (5)
O1W—Cu1—N2—C1	−81.9 (3)	C7—C8—C9—C10	0.3 (5)
N4—Cu1—N3—C10	−4.6 (2)	C6—N3—C10—C9	2.7 (5)
N2—Cu1—N3—C10	−176.9 (2)	Cu1—N3—C10—C9	−178.4 (2)
O1W—Cu1—N3—C10	94.1 (2)	C6—N3—C10—C11	−175.6 (2)
N4—Cu1—N3—C6	174.3 (2)	Cu1—N3—C10—C11	3.3 (3)
N2—Cu1—N3—C6	2.0 (2)	C8—C9—C10—N3	−1.6 (5)
O1W—Cu1—N3—C6	−86.9 (2)	C8—C9—C10—C11	176.4 (3)
O1—Cu1—N4—C15	−3.3 (3)	C15—N4—C11—C12	−1.7 (5)
N3—Cu1—N4—C15	−177.1 (3)	Cu1—N4—C11—C12	176.3 (2)
N2—Cu1—N4—C15	−156.0 (3)	C15—N4—C11—C10	177.2 (3)
O1W—Cu1—N4—C15	85.1 (3)	Cu1—N4—C11—C10	−4.8 (3)
O1—Cu1—N4—C11	178.9 (2)	N3—C10—C11—N4	1.2 (4)
N3—Cu1—N4—C11	5.1 (2)	C9—C10—C11—N4	−177.0 (3)
N2—Cu1—N4—C11	26.2 (4)	N3—C10—C11—C12	−179.9 (3)
O1W—Cu1—N4—C11	−92.7 (2)	C9—C10—C11—C12	2.0 (5)
C5—N2—C1—C2	−0.2 (5)	N4—C11—C12—C13	1.4 (5)
Cu1—N2—C1—C2	179.8 (2)	C10—C11—C12—C13	−177.4 (3)
N2—C1—C2—C3	0.6 (5)	C11—C12—C13—C14	0.3 (5)
C1—C2—C3—C4	−0.6 (5)	C12—C13—C14—C15	−1.7 (6)
C2—C3—C4—C5	0.2 (5)	C11—N4—C15—C14	0.3 (5)
C1—N2—C5—C4	−0.1 (4)	Cu1—N4—C15—C14	−177.4 (3)
Cu1—N2—C5—C4	179.9 (2)	C13—C14—C15—N4	1.5 (5)
C1—N2—C5—C6	−179.5 (3)	N4—Cu1—O1—C16	−90.9 (2)
Cu1—N2—C5—C6	0.5 (3)	N2—Cu1—O1—C16	79.3 (2)
C3—C4—C5—N2	0.1 (5)	O1W—Cu1—O1—C16	169.3 (2)
C3—C4—C5—C6	179.5 (3)	Cu1—O1—C16—O2	1.2 (4)
C10—N3—C6—C7	−2.4 (4)	Cu1—O1—C16—C17	179.5 (2)
Cu1—N3—C6—C7	178.7 (2)	O2—C16—C17—C17ⁱ	−145.5 (4)
C10—N3—C6—C5	176.6 (2)	O1—C16—C17—C17ⁱ	36.1 (5)
Cu1—N3—C6—C5	−2.3 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WB···O1ⁱⁱ	0.85	2.33	3.101 (4)	150
O2W—H2WA···O3ⁱⁱⁱ	0.85	2.32	3.138 (7)	162
O1W—H1WB···O2W	0.85	1.98	2.831 (4)	174
O1W—H1WA···O2^iv	0.85	1.92	2.755 (3)	167

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₄H₄O₄)(C₁₅H₁₁N₃)₂(H₂O)₂](NO₃)₂·2H₂O
M_r	905.77
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.397 (4), 10.650 (5), 12.574 (6)
α, β, γ (°)	70.196 (9), 83.512 (9), 83.836 (10)
V (Å³)	923.5 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.34 × 0.32 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.679, 0.724
No. of measured, independent and observed [I > 2σ(I)] reflections	4998, 3211, 2951
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.137, 0.98
No. of reflections	3211
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.67

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.917 (2)	Cu1—N2	2.049 (3)
Cu1—N3	1.937 (3)	Cu1—O1W	2.260 (2)
Cu1—N4	2.038 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WB···O1ⁱ	0.85	2.33	3.101 (4)	150.4
O2W—H2WA···O3ⁱⁱ	0.85	2.32	3.138 (7)	162.4
O1W—H1WB···O2W	0.85	1.98	2.831 (4)	173.8
O1W—H1WA···O2ⁱⁱⁱ	0.85	1.92	2.755 (3)	166.5

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

References

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Volume 66| Part 3| March 2010| Pages m346-m347

doi:10.1107/S1600536810006811

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