[μ-1,2-Bis(4-pyrid­yl)ethene-κ2N:N′]bis­[aqua­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)copper(II)] dihydrate

Lush, S.F.

doi:10.1107/S1600536811018411

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m775

doi:10.1107/S1600536811018411

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[μ-1,2-Bis(4-pyridyl)ethene-κ²N:N′]bis[aqua(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)copper(II)] dihydrate

Shie Fu Lush ^a ^*

^aGeneral Education Center, Yuanpei University, No. 306 Yuanpei St, HsinChu 30015, Taiwan
^*Correspondence e-mail: lush@mail.ypu.edu.tw

(Received 10 May 2011; accepted 15 May 2011; online 20 May 2011)

In the title dinuclear Cu^II complex, [Cu₂(C₇H₃NO₄)₂(C₁₂H₁₀N₂)(H₂O)₂]·2H₂O, the water-coordinated Cu^II cation is O,N,O′-chelated by a pyridine-2,6-dicarboxylate (pdc) dianion, and one pyridine N atom from a 1,2-bis(4-pyridyl)ethene ligand coordinates to the Cu^II cation, completing the CuN₂O₃ distorted square-pyriamidial geometry. The Cu—O_water bond [2.388 (4) Å] in the axial direction is much longer than the other Cu—O bonds. The 1,2-bis(4-pyridyl)ethene ligand is located across an inversion center with the mid-point of the C=C bond at the inversion center, and bridges two Cu^II cations, generating a centrosymmetric dinuclear complex. The crystal structure is stabilized by classical O—H⋯O and weak C—H⋯O hydrogen bonds.

Related literature

For related Cu^II complexes with pyridine-2,6-dicarboxylate ligands, see: Chaigneau et al. (2004 ); Dong et al. (2010 ); Ghosh et al. (2004 ).

Experimental

Crystal data

[Cu₂(C₇H₃NO₄)₂(C₁₂H₁₀N₂)(H₂O)₂]·2H₂O
M_r = 711.59
Triclinic, $[P \overline 1]$
a = 5.2616 (5) Å
b = 7.9316 (7) Å
c = 16.8063 (14) Å
α = 89.183 (2)°
β = 84.541 (2)°
γ = 72.557 (2)°
V = 666.01 (10) Å³
Z = 1
Mo Kα radiation
μ = 1.67 mm⁻¹
T = 295 K
0.25 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.921, T_max = 0.976
5755 measured reflections
2373 independent reflections
2174 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.126
S = 1.23
2373 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	2.388 (4)
Cu1—O2	2.053 (3)
Cu1—O4	2.003 (4)
Cu1—N1	1.902 (3)
Cu1—N2	1.951 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O6	0.82	2.10	2.669 (8)	126
O1—H1B⋯O2ⁱ	0.82	1.99	2.809 (5)	175
O6—H6A⋯O3ⁱ	0.82	2.31	2.919 (9)	132
O6—H6B⋯O3ⁱⁱ	0.82	2.06	2.851 (8)	163
C2—H2A⋯O1ⁱⁱⁱ	0.93	2.54	3.348 (6)	146
C4—H4A⋯O3^iv	0.93	2.52	3.411 (6)	160
C8—H8A⋯O1^v	0.93	2.49	3.381 (6)	161
C9—H9A⋯O5^vi	0.93	2.47	3.382 (6)	167
C13—H13A⋯O5^vii	0.93	2.35	3.265 (6)	166
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) x, y+1, z; (iv) -x, -y+2, -z+2; (v) x-1, y, z; (vi) x-1, y-1, z; (vii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018411/xu5212sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018411/xu5212Isup2.hkl

checkCIF report

Comment top

The pyridine-2,6-dicarboxylic acid (pdcH₂) has important coordination functions to transition metals by either carboxylate bridges between metal centers, to form dimeric complexes or tridentate (O, N, O') chelation to one metal ion. Some Cu^II pdc complexes have been reported (Chaigneau et al., 2004; Ghosh et al., 2004; Dong et al., 2010).

In the title compound, [Cu₂(C₁₂H₁₀N₂)(C₇H₃NO₄)₂(H₂O)₂].2(H₂O)], the Cu^II atom is coordinated by two oxygen atoms and one nitrogen atom of one pyridine-2,6-dicarboxylate (pdc) ligand, one pyrinyl N atom of the 1,2-bis(4-pyridyl)ethene ligand. The distorted square-pyriamidial geometry is completed by a longer axial bond to the O atom of a water molecule [Cu—O 2.390 (43) Å in the axial direction]. The Cu1—N2—N2ⁱ—Cu1ⁱ torsion angle is 180.0 (13)°, assemblies exhibiting M—anti-1,2-bis(4-pyridyl)ethene—M bridges. Two Cu^II atoms are bridged by one trans-1,2-bis(4-pyridyl)ethene ligand, generating a dinuclear molecule.The dinuclear molecule is located on a centre of inversion, which is in the middle of the ethylyne fragment of the bpe ligand.

The molecular structure and packing are stabilized by strong O—H···O and weak C—H···O hydrogen bonds, also including a crystal water molecule.

Related literature top

For related Cu^II complexes with pyridine-2,6-dicarboxylate ligands, see: Chaigneau et al. (2004); Dong et al. (2010); Ghosh et al. (2004).

Experimental top

A solution of Cu(NO₃)₂.6H₂O (0.296 g, 1 mmol) in 5 ml H₂O was added to pyridine-2,6-dicarboxylic acid (0.167, 1 mmol) and 1,2-bis(4-pyridyl)ethane (0.184 g, 1 mmol) in a Teflon-lined stainless steel autoclave which was heated under autogenous pressure to 453 K for 72 h and then allowed to cool to room temperature. Blue columnar crystals of the title compound were collected in 42.35% yield (based on Cu).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.[symmetry code: (i) 1 - x, -y, 1 - z].
	Fig. 2. The molecular packing for the title compound. Hydrogen bonds are shown as dashed lines.

[µ-1,2-Bis(4-pyridyl)ethene-κ²N:N']bis[aqua(pyridine- 2,6-dicarboxylato-κ³O²,N,O⁶)copper(II)] dihydrate top

Crystal data top

[Cu₂(C₇H₃NO₄)₂(C₁₂H₁₀N₂)(H₂O)₂]·2H₂O	Z = 1
M_r = 711.59	F(000) = 362
Triclinic, P1	D_x = 1.774 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2616 (5) Å	Cell parameters from 3226 reflections
b = 7.9316 (7) Å	θ = 2.5–25.0°
c = 16.8063 (14) Å	µ = 1.67 mm⁻¹
α = 89.183 (2)°	T = 295 K
β = 84.541 (2)°	Columnar, blue
γ = 72.557 (2)°	0.25 × 0.10 × 0.10 mm
V = 666.01 (10) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	2174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9 pixels mm^-1	θ_max = 25.1°, θ_min = 1.2°
ϕ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −8→9
T_min = 0.921, T_max = 0.976	l = −19→19
5755 measured reflections

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0544P)² + 0.7371P] where P = (F_o² + 2F_c²)/3
2373 reflections	(Δ/σ)_max = 0.002
200 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Cu₂(C₇H₃NO₄)₂(C₁₂H₁₀N₂)(H₂O)₂]·2H₂O	γ = 72.557 (2)°
M_r = 711.59	V = 666.01 (10) Å³
Triclinic, P1	Z = 1
a = 5.2616 (5) Å	Mo Kα radiation
b = 7.9316 (7) Å	µ = 1.67 mm⁻¹
c = 16.8063 (14) Å	T = 295 K
α = 89.183 (2)°	0.25 × 0.10 × 0.10 mm
β = 84.541 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2373 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2174 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.976	R_int = 0.036
5755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.23	Δρ_max = 0.57 e Å⁻³
2373 reflections	Δρ_min = −0.60 e Å⁻³
200 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.57285 (11)	0.65304 (7)	0.73016 (3)	0.0351 (2)
O1	0.8836 (7)	0.4653 (5)	0.8122 (2)	0.0583 (14)
O2	0.2784 (6)	0.6365 (4)	0.81661 (17)	0.0396 (10)
O3	0.0696 (7)	0.7621 (5)	0.9326 (2)	0.0557 (12)
O4	0.8504 (7)	0.7395 (4)	0.66711 (17)	0.0435 (11)
O5	1.0829 (8)	0.9308 (5)	0.6771 (2)	0.0616 (16)
N1	0.5505 (7)	0.8520 (4)	0.7953 (2)	0.0316 (11)
N2	0.5692 (7)	0.4684 (5)	0.6552 (2)	0.0343 (11)
C1	0.7125 (9)	0.9487 (6)	0.7732 (2)	0.0355 (14)
C2	0.7019 (10)	1.0950 (6)	0.8175 (3)	0.0458 (17)
C3	0.5179 (11)	1.1389 (7)	0.8849 (3)	0.0520 (17)
C4	0.3530 (10)	1.0343 (7)	0.9072 (3)	0.0478 (17)
C5	0.3772 (9)	0.8890 (6)	0.8601 (3)	0.0363 (12)
C6	0.2256 (9)	0.7535 (6)	0.8725 (3)	0.0394 (14)
C7	0.8995 (10)	0.8702 (6)	0.6991 (3)	0.0406 (16)
C8	0.4106 (10)	0.3645 (6)	0.6710 (3)	0.0431 (16)
C9	0.4046 (10)	0.2307 (6)	0.6218 (3)	0.0409 (16)
C10	0.5697 (9)	0.1958 (6)	0.5501 (2)	0.0354 (14)
C11	0.7338 (10)	0.3030 (7)	0.5338 (3)	0.0453 (16)
C12	0.7297 (10)	0.4350 (6)	0.5863 (3)	0.0434 (16)
C13	0.5754 (10)	0.0543 (6)	0.4941 (3)	0.0486 (17)
O6	0.7321 (17)	0.5326 (10)	0.9675 (4)	0.149 (4)
H1A	0.89390	0.41550	0.85540	0.0880*
H1B	0.99980	0.51510	0.81040	0.0880*
H2A	0.81460	1.16320	0.80290	0.0550*
H3A	0.50510	1.23890	0.91520	0.0620*
H4A	0.23090	1.06180	0.95240	0.0570*
H8A	0.29840	0.38510	0.71840	0.0520*
H9A	0.29080	0.16300	0.63600	0.0490*
H11A	0.84750	0.28520	0.48670	0.0540*
H12A	0.84250	0.50410	0.57390	0.0520*
H13A	0.69100	0.03930	0.44750	0.066 (17)*
H6A	0.78230	0.61090	0.98600	0.2230*
H6B	0.81680	0.44330	0.98950	0.2230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0427 (3)	0.0384 (3)	0.0323 (3)	−0.0274 (2)	0.0089 (2)	−0.0139 (2)
O1	0.052 (2)	0.048 (2)	0.082 (3)	−0.0273 (17)	0.0001 (18)	−0.0071 (18)
O2	0.0426 (18)	0.0427 (17)	0.0397 (16)	−0.0255 (14)	0.0094 (13)	−0.0145 (13)
O3	0.058 (2)	0.063 (2)	0.050 (2)	−0.0321 (18)	0.0239 (17)	−0.0156 (17)
O4	0.056 (2)	0.0483 (19)	0.0359 (16)	−0.0341 (16)	0.0111 (14)	−0.0150 (14)
O5	0.075 (3)	0.075 (3)	0.054 (2)	−0.059 (2)	0.0196 (18)	−0.0117 (18)
N1	0.0359 (19)	0.0311 (18)	0.0327 (18)	−0.0186 (16)	0.0019 (15)	−0.0067 (14)
N2	0.042 (2)	0.0353 (19)	0.0320 (18)	−0.0232 (17)	0.0040 (15)	−0.0094 (15)
C1	0.044 (3)	0.033 (2)	0.036 (2)	−0.022 (2)	−0.0013 (19)	−0.0021 (18)
C2	0.057 (3)	0.039 (3)	0.051 (3)	−0.028 (2)	−0.008 (2)	−0.003 (2)
C3	0.065 (3)	0.040 (3)	0.056 (3)	−0.025 (2)	0.002 (2)	−0.019 (2)
C4	0.054 (3)	0.049 (3)	0.041 (3)	−0.018 (2)	0.004 (2)	−0.018 (2)
C5	0.039 (2)	0.037 (2)	0.037 (2)	−0.0180 (19)	−0.0002 (18)	−0.0092 (18)
C6	0.038 (2)	0.044 (3)	0.041 (2)	−0.022 (2)	0.0053 (19)	−0.008 (2)
C7	0.052 (3)	0.045 (3)	0.034 (2)	−0.031 (2)	0.004 (2)	−0.0013 (19)
C8	0.050 (3)	0.047 (3)	0.037 (2)	−0.026 (2)	0.012 (2)	−0.015 (2)
C9	0.050 (3)	0.041 (3)	0.041 (2)	−0.031 (2)	0.008 (2)	−0.0117 (19)
C10	0.043 (3)	0.036 (2)	0.031 (2)	−0.018 (2)	−0.0008 (18)	−0.0051 (18)
C11	0.053 (3)	0.051 (3)	0.038 (2)	−0.030 (2)	0.015 (2)	−0.015 (2)
C12	0.052 (3)	0.047 (3)	0.040 (2)	−0.031 (2)	0.007 (2)	−0.011 (2)
C13	0.063 (3)	0.049 (3)	0.041 (3)	−0.033 (2)	0.015 (2)	−0.020 (2)
O6	0.195 (7)	0.159 (7)	0.095 (4)	−0.063 (6)	0.008 (5)	−0.015 (4)

Geometric parameters (Å, º) top

Cu1—O1	2.388 (4)	C2—C3	1.394 (7)
Cu1—O2	2.053 (3)	C3—C4	1.394 (8)
Cu1—O4	2.003 (4)	C4—C5	1.375 (7)
Cu1—N1	1.902 (3)	C5—C6	1.520 (7)
Cu1—N2	1.951 (4)	C8—C9	1.364 (7)
O2—C6	1.281 (6)	C9—C10	1.396 (6)
O3—C6	1.229 (6)	C10—C11	1.390 (7)
O4—C7	1.278 (6)	C10—C13	1.467 (6)
O5—C7	1.226 (7)	C11—C12	1.373 (7)
O1—H1A	0.8200	C13—C13ⁱ	1.336 (7)
O1—H1B	0.8200	C2—H2A	0.9300
O6—H6A	0.8200	C3—H3A	0.9300
O6—H6B	0.8200	C4—H4A	0.9300
N1—C1	1.333 (6)	C8—H8A	0.9300
N1—C5	1.328 (6)	C9—H9A	0.9300
N2—C12	1.346 (6)	C11—H11A	0.9300
N2—C8	1.345 (6)	C12—H12A	0.9300
C1—C2	1.372 (6)	C13—H13A	0.9300
C1—C7	1.526 (6)

O1—Cu1—O2	86.70 (12)	O3—C6—C5	119.9 (4)
O1—Cu1—O4	94.17 (13)	O2—C6—O3	125.8 (4)
O1—Cu1—N1	90.56 (14)	O2—C6—C5	114.3 (4)
O1—Cu1—N2	96.13 (14)	O4—C7—C1	114.4 (4)
O2—Cu1—O4	161.23 (12)	O5—C7—C1	119.4 (4)
O2—Cu1—N1	79.81 (14)	O4—C7—O5	126.1 (5)
O2—Cu1—N2	101.12 (14)	N2—C8—C9	124.0 (5)
O4—Cu1—N1	81.43 (14)	C8—C9—C10	119.8 (5)
O4—Cu1—N2	97.44 (14)	C11—C10—C13	120.6 (4)
N1—Cu1—N2	173.29 (15)	C9—C10—C11	116.3 (4)
Cu1—O2—C6	114.6 (3)	C9—C10—C13	123.1 (4)
Cu1—O4—C7	114.6 (3)	C10—C11—C12	120.7 (5)
H1A—O1—H1B	104.00	N2—C12—C11	122.7 (5)
Cu1—O1—H1B	101.00	C10—C13—C13ⁱ	124.0 (5)
Cu1—O1—H1A	143.00	C1—C2—H2A	121.00
H6A—O6—H6B	104.00	C3—C2—H2A	121.00
C1—N1—C5	122.9 (4)	C4—C3—H3A	120.00
Cu1—N1—C5	119.5 (3)	C2—C3—H3A	120.00
Cu1—N1—C1	117.7 (3)	C3—C4—H4A	121.00
Cu1—N2—C12	122.0 (3)	C5—C4—H4A	121.00
C8—N2—C12	116.6 (4)	C9—C8—H8A	118.00
Cu1—N2—C8	121.4 (3)	N2—C8—H8A	118.00
N1—C1—C2	120.0 (4)	C8—C9—H9A	120.00
N1—C1—C7	111.5 (4)	C10—C9—H9A	120.00
C2—C1—C7	128.5 (4)	C12—C11—H11A	120.00
C1—C2—C3	118.3 (5)	C10—C11—H11A	120.00
C2—C3—C4	120.5 (5)	N2—C12—H12A	119.00
C3—C4—C5	117.7 (5)	C11—C12—H12A	119.00
N1—C5—C4	120.6 (4)	C10—C13—H13A	118.00
N1—C5—C6	111.7 (4)	C13ⁱ—C13—H13A	118.00
C4—C5—C6	127.7 (5)

O1—Cu1—O2—C6	88.5 (3)	C1—N1—C5—C6	−178.0 (4)
N1—Cu1—O2—C6	−2.7 (3)	Cu1—N2—C8—C9	−178.3 (4)
N2—Cu1—O2—C6	−175.9 (3)	C12—N2—C8—C9	−0.1 (7)
O1—Cu1—O4—C7	−85.2 (3)	Cu1—N2—C12—C11	178.5 (4)
N1—Cu1—O4—C7	4.7 (3)	C8—N2—C12—C11	0.3 (7)
N2—Cu1—O4—C7	178.1 (3)	N1—C1—C2—C3	−0.4 (7)
O1—Cu1—N1—C1	93.5 (3)	C7—C1—C2—C3	−178.0 (5)
O1—Cu1—N1—C5	−86.4 (3)	N1—C1—C7—O4	6.8 (6)
O2—Cu1—N1—C1	−179.9 (3)	N1—C1—C7—O5	−171.0 (4)
O2—Cu1—N1—C5	0.1 (3)	C2—C1—C7—O4	−175.4 (5)
O4—Cu1—N1—C1	−0.6 (3)	C2—C1—C7—O5	6.8 (8)
O4—Cu1—N1—C5	179.5 (4)	C1—C2—C3—C4	1.2 (8)
O1—Cu1—N2—C8	84.0 (4)	C2—C3—C4—C5	−0.7 (8)
O1—Cu1—N2—C12	−94.2 (4)	C3—C4—C5—N1	−0.7 (7)
O2—Cu1—N2—C8	−3.9 (4)	C3—C4—C5—C6	178.7 (5)
O2—Cu1—N2—C12	178.0 (4)	N1—C5—C6—O2	−4.2 (6)
O4—Cu1—N2—C8	179.0 (4)	N1—C5—C6—O3	175.4 (4)
O4—Cu1—N2—C12	0.9 (4)	C4—C5—C6—O2	176.4 (5)
Cu1—O2—C6—O3	−175.2 (4)	C4—C5—C6—O3	−4.0 (8)
Cu1—O2—C6—C5	4.3 (5)	N2—C8—C9—C10	−0.2 (8)
Cu1—O4—C7—O5	170.2 (4)	C8—C9—C10—C11	0.2 (7)
Cu1—O4—C7—C1	−7.4 (5)	C8—C9—C10—C13	179.9 (5)
Cu1—N1—C1—C2	179.1 (3)	C9—C10—C11—C12	0.0 (7)
Cu1—N1—C1—C7	−2.9 (5)	C13—C10—C11—C12	−179.7 (5)
C5—N1—C1—C2	−0.9 (7)	C9—C10—C13—C13ⁱ	0.0 (8)
C5—N1—C1—C7	177.1 (4)	C11—C10—C13—C13ⁱ	179.7 (5)
Cu1—N1—C5—C4	−178.6 (4)	C10—C11—C12—N2	−0.2 (8)
Cu1—N1—C5—C6	2.0 (5)	C10—C13—C13ⁱ—C10ⁱ	180.0 (4)
C1—N1—C5—C4	1.5 (7)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6	0.82	2.10	2.669 (8)	126
O1—H1B···O2ⁱⁱ	0.82	1.99	2.809 (5)	175
O6—H6A···O3ⁱⁱ	0.82	2.31	2.919 (9)	132
O6—H6B···O3ⁱⁱⁱ	0.82	2.06	2.851 (8)	163
C2—H2A···O1^iv	0.93	2.54	3.348 (6)	146
C4—H4A···O3^v	0.93	2.52	3.411 (6)	160
C8—H8A···O1^vi	0.93	2.49	3.381 (6)	161
C9—H9A···O5^vii	0.93	2.47	3.382 (6)	167
C13—H13A···O5^viii	0.93	2.35	3.265 (6)	166

Symmetry codes: (ii) x+1, y, z; (iii) −x+1, −y+1, −z+2; (iv) x, y+1, z; (v) −x, −y+2, −z+2; (vi) x−1, y, z; (vii) x−1, y−1, z; (viii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₇H₃NO₄)₂(C₁₂H₁₀N₂)(H₂O)₂]·2H₂O
M_r	711.59
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.2616 (5), 7.9316 (7), 16.8063 (14)
α, β, γ (°)	89.183 (2), 84.541 (2), 72.557 (2)
V (Å³)	666.01 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.25 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.921, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5755, 2373, 2174
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.126, 1.23
No. of reflections	2373
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.60

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Cu1—O1	2.388 (4)	Cu1—N1	1.902 (3)
Cu1—O2	2.053 (3)	Cu1—N2	1.951 (4)
Cu1—O4	2.003 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6	0.82	2.10	2.669 (8)	126
O1—H1B···O2ⁱ	0.82	1.99	2.809 (5)	175
O6—H6A···O3ⁱ	0.82	2.31	2.919 (9)	132
O6—H6B···O3ⁱⁱ	0.82	2.06	2.851 (8)	163
C2—H2A···O1ⁱⁱⁱ	0.93	2.54	3.348 (6)	146
C4—H4A···O3^iv	0.93	2.52	3.411 (6)	160
C8—H8A···O1^v	0.93	2.49	3.381 (6)	161
C9—H9A···O5^vi	0.93	2.47	3.382 (6)	167
C13—H13A···O5^vii	0.93	2.35	3.265 (6)	166

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x, y+1, z; (iv) −x, −y+2, −z+2; (v) x−1, y, z; (vi) x−1, y−1, z; (vii) −x+2, −y+1, −z+1.

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

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