Aqua­(2,2′-bipyrimidine-κ2N,N′)(succin­ato-κ2O1,O4)copper(II) dihydrate

Ke, X.-J.; Li, D.-S.; Zhao, J.; He, Q.-F.; Li, C.

doi:10.1107/S1600536809013518

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m527

doi:10.1107/S1600536809013518

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Aqua(2,2′-bipyrimidine-κ²N,N′)(succinato-κ²O¹,O⁴)copper(II) dihydrate

Xi-Jun Ke,^a Dong-Sheng Li,^a ^* Jun Zhao,^a Qiu-Fen He ^a and Cai Li ^a

^aCollege of Mechanical and Material Engineering, Functional Materials Research Institute, China Three Gorges University, Yichang 443002, People's Republic of China
^*Correspondence e-mail: lidongsheng1@126.com

(Received 6 April 2009; accepted 9 April 2009; online 18 April 2009)

In the crystal structure of the title compound, [Cu(C₄H₄O₄)(C₈H₆N₄)(H₂O)]·2H₂O, the Cu^II atom is chelated by a 2,2′-bipyrimidine (bpm) ligand and a succinate anion in the basal plane; a water molecule in the apical position completes the slightly distorted square-pyramidal coordination geometry. Another carboxylate O atom from an adjacent complex is located in the opposite apical direction, with a Cu⋯O distance of 2.706 (3) Å, and is not considered as a bridging atom. Extensive O—H⋯O and O—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: McCann et al. (1997 ); Ray et al. (2004 ); Zhang et al. (2004 ).

Experimental

Crystal data

[Cu(C₄H₄O₄)(C₈H₆N₄)(H₂O)]·2H₂O
M_r = 391.83
Monoclinic, P 2₁ /c
a = 10.6905 (8) Å
b = 18.9321 (14) Å
c = 7.6105 (6) Å
β = 92.2290 (10)°
V = 1539.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.700, T_max = 0.877
7725 measured reflections
2735 independent reflections
2085 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.06
2735 reflections
235 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	2.386 (3)
Cu1—O2	1.918 (3)
Cu1—O5	1.940 (3)
Cu1—N1	2.017 (3)
Cu1—N2	2.012 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O1W	0.85 (4)	1.89 (4)	2.703 (5)	162 (4)
O1—H1B⋯O4ⁱ	0.85 (4)	2.05 (4)	2.903 (4)	178 (4)
O1W—H1WA⋯O2Wⁱⁱ	0.85 (4)	1.950 (17)	2.790 (6)	169 (5)
O1W—H1WB⋯N3ⁱⁱⁱ	0.84 (4)	2.45 (5)	3.216 (5)	152 (4)
O1W—H1WB⋯N4ⁱⁱⁱ	0.84 (4)	2.46 (4)	3.130 (5)	137 (5)
O2W—H2WA⋯O3ⁱⁱⁱ	0.85 (4)	2.04 (4)	2.876 (6)	167 (5)
O2W—H2WB⋯O3^iv	0.85 (4)	1.94 (4)	2.777 (5)	168 (4)
Symmetry codes: (i) -x+2, -y+2, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x, y-1, z.

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: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013518/xu2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013518/xu2509Isup2.hkl

checkCIF report

Comment top

Recently, the area of metal-organic framework materials has become one of the intense research activities for their fascinating structural diversities and potential applications in catalysis, nonlinear optics and molecular sensing. As an important family of multidentate O-donor ligands, saturated aliphatic carboxylate ligands have been extensively employed in the preparation of metal-organic complexes because of their potential properties and intriguing structural topologies (McCann et al., 1997; Ray et al., 2004; Zhang et al. 2004). Herein, we report the structure of the title complex.

The title compound contains one Cu^II cation, one suc ligands, one bpm ligands, one coordinated water and two lattice water molecules, as illustrated in Fig. 1. The Cu^II atom has a slightly distored square-pyramidal geometry (Table 1), in which the Cu^IIatom is coordinated by two N atoms of bpm ligand, two O atoms from carboxyl groups of succinate anions and one O atom from coordinated water molecule. Each unit is connected by O—H···O hydrogen bonds between carboxyl groups and coordinated water molecules (Table 2) into one-dimensional chain along c-axis. The lattice water molecule acts as both hydrogen-bond donor and acceptor. Just through hydrogen bonds (O—H···O) involving lattice water molecules, those one-dimensional chains are further connected to generate a three-dimensional supramolecular framework.

Related literature top

For general background, see: McCann et al. (1997); Ray et al. (2004); Zhang et al. (2004).

Experimental top

A mixture of CuCl₂.2H₂O (0.017 g, 0.1 mmol), bpm (0.015 g, 0.1 mmol), sodium succinate (0.0139 g, 0.1 mmol) and distilled water (10 ml) was sealed in a 25 ml Teflon-lined stainless autoclave. The pH value of the mixture was adjusted to 6 by an aqueous solution of NaOH (0.1 mol/L), and then heated at 393 K for 3 days; blue crystals were obtained on cooling to room temperature at 5 K/h.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Aqua(2,2'-bipyrimidine-κ²N,N')(succinato- κ²O¹,O⁴)copper(II) dihydrate top

Crystal data top

[Cu(C₄H₄O₄)(C₈H₆N₄)(H₂O)]·2H₂O	F(000) = 804
M_r = 391.83	D_x = 1.691 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3225 reflections
a = 10.6905 (8) Å	θ = 1.9–25.1°
b = 18.9321 (14) Å	µ = 1.46 mm⁻¹
c = 7.6105 (6) Å	T = 293 K
β = 92.229 (1)°	Prism, blue
V = 1539.2 (2) Å³	0.30 × 0.20 × 0.09 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.700, T_max = 0.877	k = −22→22
7725 measured reflections	l = −9→4

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0588P)² + 1.4777P] where P = (F_o² + 2F_c²)/3
2735 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.46 e Å⁻³
10 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Cu(C₄H₄O₄)(C₈H₆N₄)(H₂O)]·2H₂O	V = 1539.2 (2) Å³
M_r = 391.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6905 (8) Å	µ = 1.46 mm⁻¹
b = 18.9321 (14) Å	T = 293 K
c = 7.6105 (6) Å	0.30 × 0.20 × 0.09 mm
β = 92.229 (1)°

Data collection top

Bruker SMART CCD diffractometer	2735 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2085 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.877	R_int = 0.036
7725 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	10 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.46 e Å⁻³
2735 reflections	Δρ_min = −0.66 e Å⁻³
235 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	0.83883 (5)	0.98092 (2)	0.42287 (7)	0.0376 (2)
O1	0.7210 (3)	0.94912 (16)	0.1622 (4)	0.0477 (8)
H1A	0.673 (4)	0.9136 (17)	0.160 (6)	0.072*
H1B	0.774 (4)	0.945 (2)	0.082 (5)	0.072*
O1W	0.6018 (4)	0.82533 (18)	0.2132 (6)	0.0724 (11)
H1WA	0.5230 (12)	0.819 (3)	0.212 (9)	0.109*
H1WB	0.637 (4)	0.790 (2)	0.170 (9)	0.109*
O2	0.7834 (3)	1.07626 (14)	0.4543 (4)	0.0459 (7)
O2W	0.6560 (4)	0.3145 (2)	0.2485 (6)	0.0810 (12)
H2WB	0.674 (7)	0.2726 (15)	0.280 (8)	0.121*
H2WA	0.676 (7)	0.321 (3)	0.143 (4)	0.121*
O3	0.7344 (3)	1.18623 (16)	0.3913 (5)	0.0606 (9)
O4	1.1035 (3)	1.06421 (15)	0.1176 (4)	0.0490 (8)
O5	0.9903 (3)	1.00736 (14)	0.3069 (4)	0.0395 (7)
N1	0.8883 (3)	0.87826 (17)	0.4388 (4)	0.0362 (8)
N2	0.7034 (3)	0.94476 (18)	0.5757 (4)	0.0382 (8)
N3	0.8133 (3)	0.76731 (17)	0.5315 (5)	0.0468 (9)
N4	0.6295 (3)	0.8392 (2)	0.7042 (5)	0.0494 (10)
C1	0.9872 (4)	0.8470 (2)	0.3680 (6)	0.0435 (10)
H1C	1.0466	0.8745	0.3135	0.052*
C2	1.0017 (4)	0.7748 (2)	0.3750 (6)	0.0499 (11)
H2	1.0700	0.7525	0.3272	0.060*
C3	0.9102 (4)	0.7374 (2)	0.4561 (6)	0.0491 (11)
H3	0.9164	0.6884	0.4584	0.059*
C4	0.8069 (4)	0.8370 (2)	0.5194 (5)	0.0368 (9)
C5	0.7056 (4)	0.8751 (2)	0.6045 (5)	0.0376 (9)
C6	0.5436 (4)	0.8772 (3)	0.7835 (7)	0.0573 (13)
H6	0.4886	0.8539	0.8557	0.069*
C7	0.5319 (4)	0.9492 (3)	0.7641 (6)	0.0546 (12)
H7	0.4704	0.9746	0.8201	0.066*
C8	0.6163 (4)	0.9822 (2)	0.6570 (6)	0.0459 (11)
H8	0.6124	1.0309	0.6414	0.055*
C9	0.7701 (4)	1.1270 (2)	0.3460 (6)	0.0413 (10)
C10	0.7927 (4)	1.1167 (2)	0.1584 (6)	0.0442 (11)
H10A	0.7179	1.0939	0.1097	0.053*
H10B	0.7932	1.1638	0.1082	0.053*
C11	0.8904 (4)	1.0823 (2)	0.0863 (6)	0.0409 (10)
H11A	0.9243	1.1155	0.0036	0.049*
H11B	0.8523	1.0448	0.0156	0.049*
C12	1.0022 (4)	1.0491 (2)	0.1772 (5)	0.0370 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0438 (3)	0.0255 (3)	0.0444 (3)	0.0014 (2)	0.0122 (2)	0.0028 (2)
O1	0.0475 (18)	0.0452 (17)	0.0511 (19)	−0.0081 (14)	0.0088 (15)	−0.0032 (15)
O1W	0.071 (2)	0.0425 (19)	0.104 (3)	−0.0055 (18)	0.012 (2)	−0.008 (2)
O2	0.0617 (19)	0.0287 (14)	0.0479 (18)	0.0054 (14)	0.0112 (15)	0.0025 (13)
O2W	0.100 (3)	0.063 (2)	0.081 (3)	0.028 (2)	0.022 (3)	0.024 (2)
O3	0.083 (2)	0.0362 (17)	0.063 (2)	0.0214 (17)	0.0051 (19)	−0.0003 (16)
O4	0.0475 (18)	0.0434 (17)	0.057 (2)	−0.0044 (14)	0.0187 (16)	0.0048 (15)
O5	0.0417 (16)	0.0332 (14)	0.0439 (17)	−0.0001 (12)	0.0055 (13)	0.0063 (13)
N1	0.0393 (18)	0.0300 (17)	0.0395 (19)	0.0004 (15)	0.0026 (16)	−0.0003 (15)
N2	0.0403 (18)	0.0358 (18)	0.039 (2)	0.0019 (15)	0.0066 (16)	0.0009 (15)
N3	0.055 (2)	0.0281 (18)	0.057 (2)	−0.0029 (16)	0.001 (2)	0.0058 (17)
N4	0.042 (2)	0.049 (2)	0.058 (2)	−0.0074 (17)	0.0105 (19)	0.0130 (19)
C1	0.046 (2)	0.041 (2)	0.044 (2)	−0.001 (2)	0.008 (2)	−0.002 (2)
C2	0.052 (3)	0.041 (2)	0.057 (3)	0.010 (2)	0.005 (2)	−0.003 (2)
C3	0.062 (3)	0.030 (2)	0.056 (3)	0.006 (2)	0.003 (2)	−0.001 (2)
C4	0.038 (2)	0.033 (2)	0.039 (2)	−0.0051 (17)	0.0001 (19)	0.0064 (18)
C5	0.038 (2)	0.037 (2)	0.038 (2)	−0.0028 (18)	−0.0011 (19)	0.0060 (18)
C6	0.045 (3)	0.069 (3)	0.059 (3)	−0.003 (2)	0.011 (2)	0.014 (3)
C7	0.045 (3)	0.068 (3)	0.051 (3)	0.005 (2)	0.012 (2)	0.002 (3)
C8	0.050 (3)	0.042 (2)	0.046 (3)	0.010 (2)	0.005 (2)	0.002 (2)
C9	0.038 (2)	0.032 (2)	0.054 (3)	0.0007 (18)	0.006 (2)	0.001 (2)
C10	0.044 (2)	0.033 (2)	0.056 (3)	−0.0061 (19)	0.001 (2)	0.010 (2)
C11	0.050 (2)	0.031 (2)	0.042 (2)	−0.0139 (19)	0.003 (2)	0.0073 (19)
C12	0.048 (2)	0.0251 (19)	0.039 (2)	−0.0006 (18)	0.008 (2)	−0.0044 (18)

Geometric parameters (Å, º) top

Cu1—O1	2.386 (3)	N4—C5	1.323 (5)
Cu1—O2	1.918 (3)	N4—C6	1.330 (6)
Cu1—O5	1.940 (3)	C1—C2	1.376 (6)
Cu1—N1	2.017 (3)	C1—H1C	0.9300
Cu1—N2	2.012 (3)	C2—C3	1.374 (6)
O1—H1A	0.85 (4)	C2—H2	0.9300
O1—H1B	0.85 (4)	C3—H3	0.9300
O1W—H1WA	0.85 (4)	C4—C5	1.472 (6)
O1W—H1WB	0.84 (4)	C6—C7	1.377 (7)
O2—C9	1.270 (5)	C6—H6	0.9300
O2W—H2WB	0.85 (4)	C7—C8	1.388 (6)
O2W—H2WA	0.85 (4)	C7—H7	0.9300
O3—C9	1.239 (5)	C8—H8	0.9300
O4—C12	1.224 (5)	C9—C10	1.469 (6)
O5—C12	1.275 (5)	C10—C11	1.365 (5)
N1—C4	1.336 (5)	C10—H10A	0.9700
N1—C1	1.343 (5)	C10—H10B	0.9700
N2—C5	1.336 (5)	C11—C12	1.495 (6)
N2—C8	1.341 (5)	C11—H11A	0.9700
N3—C4	1.324 (5)	C11—H11B	0.9700
N3—C3	1.330 (5)

O2—Cu1—O5	94.68 (12)	N3—C4—N1	125.6 (4)
O2—Cu1—N2	90.87 (13)	N3—C4—C5	119.7 (3)
O5—Cu1—N2	169.41 (13)	N1—C4—C5	114.7 (3)
O2—Cu1—N1	168.87 (13)	N4—C5—N2	126.5 (4)
O5—Cu1—N1	93.13 (13)	N4—C5—C4	118.6 (4)
N2—Cu1—N1	80.22 (13)	N2—C5—C4	114.9 (3)
O2—Cu1—O1	100.69 (12)	N4—C6—C7	123.2 (4)
O5—Cu1—O1	96.32 (12)	N4—C6—H6	118.4
N2—Cu1—O1	91.50 (12)	C7—C6—H6	118.4
N1—Cu1—O1	86.30 (12)	C6—C7—C8	116.8 (4)
Cu1—O1—H1A	121 (4)	C6—C7—H7	121.6
Cu1—O1—H1B	106 (3)	C8—C7—H7	121.6
H1A—O1—H1B	109 (4)	N2—C8—C7	120.8 (4)
H1WA—O1W—H1WB	110 (5)	N2—C8—H8	119.6
C9—O2—Cu1	131.1 (3)	C7—C8—H8	119.6
H2WB—O2W—H2WA	110 (6)	O3—C9—O2	122.1 (4)
C12—O5—Cu1	128.5 (3)	O3—C9—C10	117.0 (4)
C4—N1—C1	117.6 (3)	O2—C9—C10	120.9 (4)
C4—N1—Cu1	114.7 (3)	C11—C10—C9	127.7 (4)
C1—N1—Cu1	127.5 (3)	C11—C10—H10A	105.4
C5—N2—C8	117.0 (4)	C9—C10—H10A	105.4
C5—N2—Cu1	115.0 (3)	C11—C10—H10B	105.4
C8—N2—Cu1	128.0 (3)	C9—C10—H10B	105.4
C4—N3—C3	115.7 (4)	H10A—C10—H10B	106.0
C5—N4—C6	115.7 (4)	C10—C11—C12	128.7 (4)
N1—C1—C2	120.7 (4)	C10—C11—H11A	105.1
N1—C1—H1C	119.6	C12—C11—H11A	105.1
C2—C1—H1C	119.6	C10—C11—H11B	105.1
C3—C2—C1	116.7 (4)	C12—C11—H11B	105.1
C3—C2—H2	121.7	H11A—C11—H11B	105.9
C1—C2—H2	121.7	O4—C12—O5	123.2 (4)
N3—C3—C2	123.6 (4)	O4—C12—C11	115.7 (4)
N3—C3—H3	118.2	O5—C12—C11	121.1 (4)
C2—C3—H3	118.2

O5—Cu1—O2—C9	51.3 (4)	C3—N3—C4—C5	−177.7 (4)
N2—Cu1—O2—C9	−137.8 (4)	C1—N1—C4—N3	−2.0 (6)
N1—Cu1—O2—C9	−174.3 (6)	Cu1—N1—C4—N3	173.5 (4)
O1—Cu1—O2—C9	−46.1 (4)	C1—N1—C4—C5	176.0 (4)
O2—Cu1—O5—C12	−50.4 (3)	Cu1—N1—C4—C5	−8.5 (4)
N2—Cu1—O5—C12	−171.8 (6)	C6—N4—C5—N2	−0.5 (7)
N1—Cu1—O5—C12	137.5 (3)	C6—N4—C5—C4	177.1 (4)
O1—Cu1—O5—C12	50.9 (3)	C8—N2—C5—N4	0.7 (6)
O2—Cu1—N1—C4	43.9 (8)	Cu1—N2—C5—N4	177.8 (3)
O5—Cu1—N1—C4	178.4 (3)	C8—N2—C5—C4	−177.1 (4)
N2—Cu1—N1—C4	6.7 (3)	Cu1—N2—C5—C4	0.0 (5)
O1—Cu1—N1—C4	−85.5 (3)	N3—C4—C5—N4	5.8 (6)
O2—Cu1—N1—C1	−141.1 (6)	N1—C4—C5—N4	−172.3 (4)
O5—Cu1—N1—C1	−6.6 (4)	N3—C4—C5—N2	−176.3 (4)
N2—Cu1—N1—C1	−178.3 (4)	N1—C4—C5—N2	5.6 (5)
O1—Cu1—N1—C1	89.5 (4)	C5—N4—C6—C7	0.5 (7)
O2—Cu1—N2—C5	−176.8 (3)	N4—C6—C7—C8	−0.6 (8)
O5—Cu1—N2—C5	−55.1 (8)	C5—N2—C8—C7	−0.8 (6)
N1—Cu1—N2—C5	−3.5 (3)	Cu1—N2—C8—C7	−177.4 (3)
O1—Cu1—N2—C5	82.5 (3)	C6—C7—C8—N2	0.8 (7)
O2—Cu1—N2—C8	0.0 (4)	Cu1—O2—C9—O3	−178.8 (3)
O5—Cu1—N2—C8	121.6 (7)	Cu1—O2—C9—C10	3.2 (6)
N1—Cu1—N2—C8	173.2 (4)	O3—C9—C10—C11	137.1 (5)
O1—Cu1—N2—C8	−100.8 (4)	O2—C9—C10—C11	−44.9 (7)
C4—N1—C1—C2	1.6 (6)	C9—C10—C11—C12	−3.2 (7)
Cu1—N1—C1—C2	−173.3 (3)	Cu1—O5—C12—O4	177.3 (3)
N1—C1—C2—C3	0.5 (7)	Cu1—O5—C12—C11	−3.5 (5)
C4—N3—C3—C2	2.2 (7)	C10—C11—C12—O4	−131.7 (4)
C1—C2—C3—N3	−2.5 (7)	C10—C11—C12—O5	49.0 (6)
C3—N3—C4—N1	0.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1W	0.85 (4)	1.89 (4)	2.703 (5)	162 (4)
O1—H1B···O4ⁱ	0.85 (4)	2.05 (4)	2.903 (4)	178 (4)
O1W—H1WA···O2Wⁱⁱ	0.85 (4)	1.95 (2)	2.790 (6)	169 (5)
O1W—H1WB···N3ⁱⁱⁱ	0.84 (4)	2.45 (5)	3.216 (5)	152 (4)
O1W—H1WB···N4ⁱⁱⁱ	0.84 (4)	2.46 (4)	3.130 (5)	137 (5)
O2W—H2WA···O3ⁱⁱⁱ	0.85 (4)	2.04 (4)	2.876 (6)	167 (5)
O2W—H2WB···O3^iv	0.85 (4)	1.94 (4)	2.777 (5)	168 (4)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₄H₄O₄)(C₈H₆N₄)(H₂O)]·2H₂O
M_r	391.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.6905 (8), 18.9321 (14), 7.6105 (6)
β (°)	92.229 (1)
V (Å³)	1539.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.30 × 0.20 × 0.09

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.700, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	7725, 2735, 2085
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.06
No. of reflections	2735
No. of parameters	235
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.66

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	2.386 (3)	Cu1—N1	2.017 (3)
Cu1—O2	1.918 (3)	Cu1—N2	2.012 (3)
Cu1—O5	1.940 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1W	0.85 (4)	1.89 (4)	2.703 (5)	162 (4)
O1—H1B···O4ⁱ	0.85 (4)	2.05 (4)	2.903 (4)	178 (4)
O1W—H1WA···O2Wⁱⁱ	0.85 (4)	1.950 (17)	2.790 (6)	169 (5)
O1W—H1WB···N3ⁱⁱⁱ	0.84 (4)	2.45 (5)	3.216 (5)	152 (4)
O1W—H1WB···N4ⁱⁱⁱ	0.84 (4)	2.46 (4)	3.130 (5)	137 (5)
O2W—H2WA···O3ⁱⁱⁱ	0.85 (4)	2.04 (4)	2.876 (6)	167 (5)
O2W—H2WB···O3^iv	0.85 (4)	1.94 (4)	2.777 (5)	168 (4)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, y−1, z.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant No. 20773104), the Program for New Century Excellent Talents in Universities (NCET-06-0891), the Natural Science Foundation of Hubei/Shaanxi Provinces of China (2008CDB030) and the Important Project of Hubei Provincial Education Office, China (Z20091301).

References

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