catena-Poly[[[aqua­(2,2′-bipyridine-κ2N,N′)copper(II)]-μ-furan-2,5-di­carboxyl­ato-κ2O2:O5] dihydrate]

Li, Y.-F.; Xu, Y.; Qin, X.-L.; Yuan, Y.-P.; Gao, W.-Y.

doi:10.1107/S1600536812043632

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1416

doi:10.1107/S1600536812043632

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catena-Poly[[[aqua(2,2′-bipyridine-κ²N,N′)copper(II)]-μ-furan-2,5-dicarboxylato-κ²O²:O⁵] dihydrate]

Ya-Feng Li,^a ^* Yue Xu,^a Xiao-Lin Qin,^a Yong-Peng Yuan ^a and Wen-Yuan Gao ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: fly012345@sohu.com

(Received 15 October 2012; accepted 21 October 2012; online 27 October 2012)

In the crystal structure of the title compound, {[Cu(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O}_n, an infinite chain parallel to [110] is formed by the linking of Cu(H₂O)(2,2′-bipyridine) units through a furan-2,5-dicarboxylate bridge. The Cu^II atom shows a square-pyramidal geometry, with one furan-2,5-dicarboxylate O atom in the apical position. The dihedral angle between the planes of the furan ring and the bipyridine molecule is 83.88 (7)°. O_water—H⋯O hydrogen bonds connect adjacent chains, generating a layer motif parallel to (001).

Related literature

For a related structure, see: Li et al. (2012 ).

Experimental

Crystal data

[Cu(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O
M_r = 427.86
Triclinic, $[P \overline 1]$
a = 8.8621 (18) Å
b = 8.9016 (18) Å
c = 12.523 (3) Å
α = 88.33 (3)°
β = 69.31 (3)°
γ = 66.85 (3)°
V = 842.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.589, T_max = 0.738
8312 measured reflections
3809 independent reflections
3430 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.09
3809 reflections
262 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O1ⁱ	0.86 (2)	1.87 (2)	2.676 (2)	156 (2)
O1W—H1B⋯O4ⁱⁱ	0.86 (2)	1.78 (2)	2.623 (2)	166 (2)
O2W—H2A⋯O5	0.86 (2)	2.42 (3)	3.211 (4)	153 (4)
O2W—H2B⋯O2	0.87 (2)	2.59 (3)	3.353 (4)	146 (4)
O3W—H3A⋯O4ⁱⁱⁱ	0.86 (2)	2.10 (2)	2.891 (3)	153 (4)
O3W—H3B⋯O2	0.87 (2)	1.96 (2)	2.797 (3)	162 (4)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043632/ng5302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043632/ng5302Isup2.hkl

checkCIF report

Comment top

Recently, we utilized furan-2,5-dicarboxyl acid as the ligand to construct coordination polymers (Li et al., 2012). As an extension of this work, a chainlike compound, [Cu(H₂O)(C₁₀H₈N₂)(C₆H₂O₅)]^.2H₂O (I), is now determined.

The asymmetric unit of (I) is consisted of one Cu(II) cation, one furan-2,5-dicarboxylate anion, one 2,2'-bipyridine and three water molecule The Cu atom is coordinated by two N atoms of 2,2'-bipyridine, one water O atoms and two carboxylate O atoms, exhibiting distorted square pyramid. Adjacent Cu atoms are connected by the furan-2,5-dicarboxylate to form an infinite chain (Fig. 2); O_water—H···O hydrogen bonds hold together ajacent chains to form a layer motif (Fig. 3).

Related literature top

For a related structure, see: Li et al. (2012).

Experimental top

Furan-2,5-dicarboxyl acid (0.0156 g, 0.10 mmol), Cu(NO₃)₂^.6H₂O (0.0298 g, 0.10 mmol), 2,2'-bipyridine (0.0156, 0.10 mmol) and NaOH (0.004, 0.10 mmol) were dissolved in water (5 ml, 278 mmol) under stirring. The mixture with molar ratio of 1 (furan-2,5-dicarboxyl acid): 1 (Cu(NO₃)₂^.6H₂O): 1 (2,2'-bipyridine): 1 NaOH: 2780 H₂O was layed under room temperature for 5 days. Blue blocks were collected as a single phase.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: Crystal Structure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The unit cell of (I), showing the atomic labelling scheme and displacement ellipsoids at the 50% probability level. [Symmetry codes: (i) -1 + x, 1 + y, z.]
	Fig. 2. Polyhedral plot of (I), displaying the infinite chain formed by linking the adjacent Cu cations with furan-2,5-dicarboxylate.
	Fig. 3. Ball-stick packing diagram of (I). The adjacent chains are holded together by the O_water–H···O H-bonding interactions to the supermolecular net.

catena-Poly[[[aqua(2,2'-bipyridine-κ²N,N')copper(II)]- µ-furan-2,5-dicarboxylato-κ²O²:O⁵] dihydrate] top

Crystal data top

[Cu(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O	Z = 2
M_r = 427.86	F(000) = 438
Triclinic, P1	D_x = 1.686 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8621 (18) Å	Cell parameters from 2000 reflections
b = 8.9016 (18) Å	θ = 3.2–27.5°
c = 12.523 (3) Å	µ = 1.35 mm⁻¹
α = 88.33 (3)°	T = 293 K
β = 69.31 (3)°	Block, blue
γ = 66.85 (3)°	0.44 × 0.40 × 0.24 mm
V = 842.8 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3809 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→11
T_min = 0.589, T_max = 0.738	l = −16→16
8312 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0544P)² + 0.2206P] where P = (F_o² + 2F_c²)/3
3809 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.38 e Å⁻³
8 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Cu(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O	γ = 66.85 (3)°
M_r = 427.86	V = 842.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.8621 (18) Å	Mo Kα radiation
b = 8.9016 (18) Å	µ = 1.35 mm⁻¹
c = 12.523 (3) Å	T = 293 K
α = 88.33 (3)°	0.44 × 0.40 × 0.24 mm
β = 69.31 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3809 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3430 reflections with I > 2σ(I)
T_min = 0.589, T_max = 0.738	R_int = 0.022
8312 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	8 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.38 e Å⁻³
3809 reflections	Δρ_min = −0.60 e Å⁻³
262 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.11580 (3)	1.01038 (3)	0.296968 (19)	0.02954 (10)
O1	0.15473 (18)	0.80049 (16)	0.36822 (12)	0.0331 (3)
O2	0.4389 (2)	0.7287 (2)	0.26090 (15)	0.0451 (4)
O3	0.53028 (17)	0.43934 (16)	0.35228 (12)	0.0293 (3)
O4	0.6968 (2)	0.0548 (2)	0.45196 (17)	0.0512 (4)
O5	0.8433 (2)	0.19001 (19)	0.33789 (14)	0.0428 (4)
N1	0.1301 (2)	0.9088 (2)	0.15292 (15)	0.0326 (4)
N2	0.2242 (2)	1.1413 (2)	0.18474 (14)	0.0312 (3)
C1	0.3191 (3)	0.7013 (2)	0.33247 (16)	0.0288 (4)
C2	0.3569 (2)	0.5458 (2)	0.38399 (16)	0.0261 (4)
C3	0.2525 (3)	0.4845 (2)	0.46097 (19)	0.0335 (4)
H3	0.1299	0.5339	0.4956	0.040*
C4	0.3660 (3)	0.3303 (3)	0.4786 (2)	0.0366 (4)
H4	0.3327	0.2579	0.5265	0.044*
C5	0.5319 (3)	0.3088 (2)	0.41239 (17)	0.0294 (4)
C6	0.7064 (3)	0.1739 (2)	0.39860 (18)	0.0338 (4)
C7	0.0776 (3)	0.7887 (3)	0.1463 (2)	0.0421 (5)
H7	0.0250	0.7516	0.2136	0.050*
C8	0.0994 (4)	0.7183 (3)	0.0416 (2)	0.0478 (6)
H8	0.0612	0.6357	0.0385	0.057*
C9	0.1790 (3)	0.7732 (3)	−0.0579 (2)	0.0486 (6)
H9	0.1979	0.7257	−0.1292	0.058*
C10	0.2306 (3)	0.8992 (3)	−0.05098 (19)	0.0416 (5)
H10	0.2828	0.9386	−0.1172	0.050*
C11	0.2033 (3)	0.9656 (2)	0.05623 (17)	0.0320 (4)
C12	0.2515 (3)	1.1018 (2)	0.07481 (17)	0.0310 (4)
C13	0.3209 (3)	1.1829 (3)	−0.01247 (19)	0.0409 (5)
H13	0.3389	1.1543	−0.0882	0.049*
C14	0.3626 (3)	1.3065 (3)	0.0148 (2)	0.0455 (5)
H14	0.4086	1.3629	−0.0424	0.055*
C15	0.3359 (3)	1.3460 (3)	0.1276 (2)	0.0439 (5)
H15	0.3648	1.4284	0.1472	0.053*
C16	0.2659 (3)	1.2617 (3)	0.2105 (2)	0.0398 (5)
H16	0.2468	1.2889	0.2867	0.048*
O1W	0.1177 (2)	1.12059 (17)	0.43017 (12)	0.0325 (3)
H1A	0.014 (2)	1.164 (3)	0.4834 (19)	0.039*
H1B	0.191 (3)	1.056 (3)	0.458 (2)	0.039*
O2W	0.8652 (4)	0.5101 (4)	0.2205 (3)	0.0910 (9)
H2A	0.832 (6)	0.451 (5)	0.272 (3)	0.109*
H2B	0.767 (4)	0.599 (4)	0.241 (4)	0.109*
O3W	0.6105 (5)	0.9237 (5)	0.2840 (2)	0.1073 (12)
H3A	0.611 (7)	0.952 (6)	0.349 (3)	0.129*
H3B	0.540 (6)	0.876 (6)	0.291 (4)	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03370 (15)	0.02750 (14)	0.02279 (14)	−0.00666 (10)	−0.01233 (10)	0.00782 (9)
O1	0.0304 (7)	0.0281 (6)	0.0285 (7)	−0.0017 (5)	−0.0093 (6)	0.0085 (5)
O2	0.0393 (9)	0.0437 (9)	0.0430 (9)	−0.0158 (7)	−0.0071 (7)	0.0168 (7)
O3	0.0238 (6)	0.0268 (6)	0.0306 (7)	−0.0038 (5)	−0.0104 (5)	0.0055 (5)
O4	0.0553 (11)	0.0374 (8)	0.0717 (12)	−0.0114 (7)	−0.0454 (10)	0.0227 (8)
O5	0.0294 (8)	0.0399 (8)	0.0448 (9)	0.0019 (6)	−0.0154 (7)	0.0012 (6)
N1	0.0358 (9)	0.0294 (8)	0.0298 (9)	−0.0069 (7)	−0.0167 (7)	0.0074 (6)
N2	0.0314 (8)	0.0318 (8)	0.0245 (8)	−0.0078 (7)	−0.0098 (7)	0.0066 (6)
C1	0.0322 (10)	0.0252 (8)	0.0258 (9)	−0.0070 (7)	−0.0127 (8)	0.0042 (7)
C2	0.0230 (8)	0.0244 (8)	0.0271 (9)	−0.0037 (6)	−0.0116 (7)	0.0025 (7)
C3	0.0257 (9)	0.0316 (9)	0.0396 (11)	−0.0084 (7)	−0.0121 (8)	0.0099 (8)
C4	0.0370 (11)	0.0322 (10)	0.0431 (12)	−0.0133 (8)	−0.0192 (9)	0.0160 (8)
C5	0.0314 (10)	0.0254 (8)	0.0318 (10)	−0.0063 (7)	−0.0184 (8)	0.0058 (7)
C6	0.0356 (11)	0.0290 (9)	0.0349 (11)	−0.0025 (8)	−0.0228 (9)	−0.0001 (7)
C7	0.0499 (13)	0.0355 (11)	0.0435 (13)	−0.0141 (9)	−0.0246 (11)	0.0110 (9)
C8	0.0538 (14)	0.0353 (11)	0.0593 (16)	−0.0112 (10)	−0.0343 (13)	0.0032 (10)
C9	0.0499 (14)	0.0471 (13)	0.0412 (13)	−0.0049 (10)	−0.0247 (11)	−0.0062 (10)
C10	0.0378 (11)	0.0467 (12)	0.0291 (11)	−0.0050 (9)	−0.0134 (9)	0.0008 (9)
C11	0.0265 (9)	0.0326 (9)	0.0278 (10)	−0.0014 (7)	−0.0123 (8)	0.0040 (7)
C12	0.0255 (9)	0.0337 (9)	0.0246 (9)	−0.0028 (7)	−0.0096 (8)	0.0056 (7)
C13	0.0409 (12)	0.0465 (12)	0.0253 (10)	−0.0117 (9)	−0.0086 (9)	0.0099 (8)
C14	0.0428 (13)	0.0471 (12)	0.0382 (12)	−0.0167 (10)	−0.0082 (10)	0.0157 (10)
C15	0.0453 (13)	0.0410 (12)	0.0443 (13)	−0.0194 (10)	−0.0141 (11)	0.0111 (9)
C16	0.0459 (12)	0.0402 (11)	0.0329 (11)	−0.0168 (9)	−0.0154 (10)	0.0074 (8)
O1W	0.0319 (7)	0.0338 (7)	0.0247 (7)	−0.0049 (6)	−0.0125 (6)	0.0064 (5)
O2W	0.0754 (18)	0.0805 (18)	0.091 (2)	−0.0308 (14)	−0.0024 (16)	0.0061 (15)
O3W	0.166 (3)	0.179 (3)	0.0414 (12)	−0.140 (3)	−0.0327 (16)	0.0241 (16)

Geometric parameters (Å, º) top

Cu1—O1W	1.9681 (15)	C7—H7	0.9300
Cu1—N1	1.9825 (18)	C8—C9	1.380 (4)
Cu1—O1	2.0048 (15)	C8—H8	0.9300
Cu1—N2	2.0218 (18)	C9—C10	1.382 (4)
Cu1—O5ⁱ	2.1885 (18)	C9—H9	0.9300
O1—C1	1.286 (2)	C10—C11	1.384 (3)
O2—C1	1.228 (3)	C10—H10	0.9300
O3—C5	1.364 (2)	C11—C12	1.483 (3)
O3—C2	1.364 (2)	C12—C13	1.386 (3)
O4—C6	1.252 (3)	C13—C14	1.377 (4)
O5—C6	1.244 (3)	C13—H13	0.9300
N1—C7	1.338 (3)	C14—C15	1.378 (4)
N1—C11	1.345 (3)	C14—H14	0.9300
N2—C12	1.343 (3)	C15—C16	1.376 (3)
N2—C16	1.343 (3)	C15—H15	0.9300
C1—C2	1.477 (2)	C16—H16	0.9300
C2—C3	1.349 (3)	O1W—H1A	0.861 (15)
C3—C4	1.413 (3)	O1W—H1B	0.856 (16)
C3—H3	0.9300	O2W—H2A	0.862 (19)
C4—C5	1.346 (3)	O2W—H2B	0.872 (19)
C4—H4	0.9300	O3W—H3A	0.862 (18)
C5—C6	1.493 (3)	O3W—H3B	0.868 (18)
C7—C8	1.386 (3)

O1W—Cu1—N1	174.26 (7)	O5—C6—C5	118.49 (19)
O1W—Cu1—O1	91.08 (6)	O5—C6—C5	118.49 (19)
N1—Cu1—O1	92.85 (7)	O4—C6—C5	114.5 (2)
O1W—Cu1—N2	93.35 (7)	N1—C7—C8	121.7 (2)
N1—Cu1—N2	81.09 (7)	N1—C7—H7	119.1
O1—Cu1—N2	147.26 (7)	C8—C7—H7	119.1
O1W—Cu1—O5ⁱ	88.22 (7)	C9—C8—C7	118.8 (2)
N1—Cu1—O5ⁱ	93.61 (8)	C9—C8—H8	120.6
O1—Cu1—O5ⁱ	117.97 (7)	C7—C8—H8	120.6
N2—Cu1—O5ⁱ	94.59 (7)	C8—C9—C10	119.6 (2)
C1—O1—Cu1	112.08 (13)	C8—C9—H9	120.2
C5—O3—C2	106.11 (15)	C10—C9—H9	120.2
C6—O5—Cu1ⁱⁱ	126.72 (14)	C9—C10—C11	118.9 (2)
C7—N1—C11	119.63 (18)	C9—C10—H10	120.6
C7—N1—Cu1	124.99 (15)	C11—C10—H10	120.6
C11—N1—Cu1	115.35 (14)	N1—C11—C10	121.4 (2)
C12—N2—C16	119.17 (18)	N1—C11—C12	114.70 (17)
C12—N2—Cu1	114.27 (14)	C10—C11—C12	123.9 (2)
C16—N2—Cu1	126.55 (14)	N2—C12—C13	121.52 (19)
O2—C1—O1	124.51 (18)	N2—C12—C11	114.49 (18)
O2—C1—O1	124.51 (18)	C13—C12—C11	124.00 (18)
O2—C1—C2	120.80 (18)	C14—C13—C12	118.9 (2)
O2—C1—C2	120.80 (18)	C14—C13—H13	120.6
O1—C1—C2	114.69 (17)	C12—C13—H13	120.6
C3—C2—O3	110.33 (16)	C13—C14—C15	119.6 (2)
C3—C2—C1	132.79 (17)	C13—C14—H14	120.2
O3—C2—C1	116.87 (17)	C15—C14—H14	120.2
C2—C3—C4	106.52 (18)	C16—C15—C14	118.9 (2)
C2—C3—H3	126.7	C16—C15—H15	120.6
C4—C3—H3	126.7	C14—C15—H15	120.6
C5—C4—C3	106.56 (19)	N2—C16—C15	122.0 (2)
C5—C4—H4	126.7	N2—C16—H16	119.0
C3—C4—H4	126.7	C15—C16—H16	119.0
C4—C5—O3	110.48 (17)	Cu1—O1W—H1A	111.7 (16)
C4—C5—C6	131.21 (19)	Cu1—O1W—H1B	112.7 (16)
O3—C5—C6	118.28 (18)	H1A—O1W—H1B	109.8 (19)
O5—C6—O4	127.0 (2)	H2A—O2W—H2B	100 (4)
O5—C6—O4	127.0 (2)	H3A—O3W—H3B	113 (3)

O1W—Cu1—O1—C1	−95.25 (14)	Cu1ⁱⁱ—O5—C6—O5	0 (100)
N1—Cu1—O1—C1	80.57 (14)	O5—O5—C6—O4	0.00 (8)
N2—Cu1—O1—C1	2.6 (2)	Cu1ⁱⁱ—O5—C6—O4	2.9 (3)
O5ⁱ—Cu1—O1—C1	176.19 (12)	O5—O5—C6—C5	0.00 (6)
O1—Cu1—N1—C7	32.30 (18)	Cu1ⁱⁱ—O5—C6—C5	−177.61 (12)
N2—Cu1—N1—C7	179.94 (18)	C4—C5—C6—O5	−174.2 (2)
O5ⁱ—Cu1—N1—C7	−85.97 (18)	O3—C5—C6—O5	3.8 (3)
O1—Cu1—N1—C11	−145.90 (14)	C4—C5—C6—O5	−174.2 (2)
N2—Cu1—N1—C11	1.74 (14)	O3—C5—C6—O5	3.8 (3)
O5ⁱ—Cu1—N1—C11	95.83 (15)	C4—C5—C6—O4	5.4 (3)
O1W—Cu1—N2—C12	178.94 (14)	O3—C5—C6—O4	−176.59 (17)
N1—Cu1—N2—C12	0.37 (14)	C11—N1—C7—C8	1.2 (3)
O1—Cu1—N2—C12	81.71 (18)	Cu1—N1—C7—C8	−176.89 (17)
O5ⁱ—Cu1—N2—C12	−92.58 (14)	N1—C7—C8—C9	0.6 (4)
O1W—Cu1—N2—C16	−2.47 (18)	C7—C8—C9—C10	−1.7 (4)
N1—Cu1—N2—C16	178.95 (19)	C8—C9—C10—C11	1.0 (3)
O1—Cu1—N2—C16	−99.7 (2)	C7—N1—C11—C10	−2.0 (3)
O5ⁱ—Cu1—N2—C16	86.00 (18)	Cu1—N1—C11—C10	176.33 (15)
O2—O2—C1—O1	0.00 (8)	C7—N1—C11—C12	178.33 (18)
O2—O2—C1—C2	0.00 (14)	Cu1—N1—C11—C12	−3.4 (2)
Cu1—O1—C1—O2	−1.8 (3)	C9—C10—C11—N1	0.9 (3)
Cu1—O1—C1—O2	−1.8 (3)	C9—C10—C11—C12	−179.47 (19)
Cu1—O1—C1—C2	178.61 (12)	C16—N2—C12—C13	−0.3 (3)
C5—O3—C2—C3	−0.3 (2)	Cu1—N2—C12—C13	178.40 (16)
C5—O3—C2—C1	178.50 (15)	C16—N2—C12—C11	179.10 (17)
O2—C1—C2—C3	−178.6 (2)	Cu1—N2—C12—C11	−2.2 (2)
O2—C1—C2—C3	−178.6 (2)	N1—C11—C12—N2	3.7 (2)
O1—C1—C2—C3	1.1 (3)	C10—C11—C12—N2	−176.01 (19)
O2—C1—C2—O3	2.9 (3)	N1—C11—C12—C13	−176.94 (19)
O2—C1—C2—O3	2.9 (3)	C10—C11—C12—C13	3.4 (3)
O1—C1—C2—O3	−177.42 (16)	N2—C12—C13—C14	0.1 (3)
O3—C2—C3—C4	−0.2 (2)	C11—C12—C13—C14	−179.3 (2)
C1—C2—C3—C4	−178.8 (2)	C12—C13—C14—C15	0.5 (3)
C2—C3—C4—C5	0.7 (2)	C13—C14—C15—C16	−0.8 (4)
C3—C4—C5—O3	−0.9 (2)	C12—N2—C16—C15	0.0 (3)
C3—C4—C5—C6	177.18 (19)	Cu1—N2—C16—C15	−178.54 (18)
C2—O3—C5—C4	0.8 (2)	C14—C15—C16—N2	0.5 (4)
C2—O3—C5—C6	−177.60 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1ⁱⁱⁱ	0.86 (2)	1.87 (2)	2.676 (2)	156 (2)
O1W—H1B···O4^iv	0.86 (2)	1.78 (2)	2.623 (2)	166 (2)
O2W—H2A···O5	0.86 (2)	2.42 (3)	3.211 (4)	153 (4)
O2W—H2B···O2	0.87 (2)	2.59 (3)	3.353 (4)	146 (4)
O3W—H3A···O4^v	0.86 (2)	2.10 (2)	2.891 (3)	153 (4)
O3W—H3B···O2	0.87 (2)	1.96 (2)	2.797 (3)	162 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₆H₂O₅)(C₁₀H₈N₂)(H₂O)]·2H₂O
M_r	427.86
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8621 (18), 8.9016 (18), 12.523 (3)
α, β, γ (°)	88.33 (3), 69.31 (3), 66.85 (3)
V (Å³)	842.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.44 × 0.40 × 0.24

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.589, 0.738
No. of measured, independent and observed [I > 2σ(I)] reflections	8312, 3809, 3430
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.09
No. of reflections	3809
No. of parameters	262
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.60

Computer programs: PROCESS-AUTO (Rigaku, 1998), Crystal Structure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1ⁱ	0.861 (15)	1.867 (19)	2.676 (2)	156 (2)
O1W—H1B···O4ⁱⁱ	0.856 (16)	1.783 (17)	2.623 (2)	166 (2)
O2W—H2A···O5	0.862 (19)	2.42 (3)	3.211 (4)	153 (4)
O2W—H2B···O2	0.872 (19)	2.59 (3)	3.353 (4)	146 (4)
O3W—H3A···O4ⁱⁱⁱ	0.862 (18)	2.10 (2)	2.891 (3)	153 (4)
O3W—H3B···O2	0.868 (18)	1.96 (2)	2.797 (3)	162 (4)

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

Acknowledgements

This project was sponsored by the Scientific Research Foundation for the Returned Overseas Team, Chinese Education Ministry.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, Y.-F., Xu, Y., Qin, X.-L., Yuan, Y.-P. & Gao, W.-Y. (2012). Acta Cryst. E68, m1140. CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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