catena-Poly[[aqua­bis­(N6-benzyl­adenine-κN3)copper(II)]-μ-benzene-1,4-dicarboxyl­ato-κ2O1:O4]

Li, W.-B.

doi:10.1107/S1600536811032168

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1249-m1250

doi:10.1107/S1600536811032168

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catena-Poly[[aquabis(N⁶-benzyladenine-κN³)copper(II)]-μ-benzene-1,4-dicarboxylato-κ²O¹:O⁴]

Wen-Bo Li ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou, Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzwbli@163.com

(Received 16 July 2011; accepted 8 August 2011; online 17 August 2011)

In the title compound, [Cu(C₈H₄O₄)(C₁₂H₁₁N₅)₂(H₂O)]_n, the Cu^II ion is five-coordinated by two carboxylate O atoms from two symmetry-related benzene-1,4-dicarboxylate ligands, two N atoms from two symmetry-related N⁶-benzyladenine ligands and one water O atom in a square-pyramidal environment. The Cu^II and water O atoms lie on a twofold rotation axis, and the benzene-1,4-dicarboxylate ligand lies on an inversion center. The water O atom occupies the apical position and the basal plane is occupied by two O atoms and two N atoms. Each benzene-1,4-dicarboxylate anion acts as a bis-monodentate ligand that binds two Cu^II cations, forming an infinite chain extending parallel to [001]. The N⁶-benzyladenine ligands are attached on both sides of the chain. Neighboring chains are further interconnected into the resulting three-dimensional supramolecular architecture via O—H⋯O, N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For examples of the use of biomolecules in metal-organic frameworks, see: An et al. (2009 ); Lee et al. (2008 ); Xie et al. (2007 ).

Experimental

Crystal data

[Cu(C₈H₄O₄)(C₁₂H₁₁N₅)₂(H₂O)]
M_r = 696.18
Monoclinic, C 2/c
a = 28.171 (2) Å
b = 5.554 (1) Å
c = 22.102 (1) Å
β = 115.868 (1)°
V = 3111.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.884, T_max = 0.897
7556 measured reflections
2744 independent reflections
2455 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.03
2744 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2ⁱ	0.86	1.80	2.6388 (17)	164
N6—H6⋯O2ⁱⁱ	0.85	2.07	2.855 (2)	154
N8—H8⋯N7ⁱⁱⁱ	0.86	2.20	3.018 (3)	160
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+1, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032168/nk2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032168/nk2102Isup2.hkl

checkCIF report

Comment top

Recently, biomolecules such as 2-amino-3-(4-aminophenyl)-propionic acid (Xie et al., 2007), glycine and alanine(Lee et al., 2008) and adenine (An et al., 2009) were used to construct metal-organic frameworks (MOFs) due potential biomedical usefulness. During the synthesis of bio-MOFs using a biomolecule and Cu^II ion, the title compound (I) was obtained, and here its crystal structure is reported.

The asymmetric unit of (I) is composed of one Cu^II cation, one N⁶-benzyladenine molecule, half of benzene-1,4-dicarboxylate anion and one water molecule. As shown in Figure 1, the Cu^II ion is five-coordinated by two carboxylate O atoms from two different benzene-1,4-dicarboxylate ligands, two N atoms from two different N⁶-benzyladenine ligands and one water O atom in a square-pyramidal coordination environment. The Cu^II and water O atoms lie on a twofold rotation axis, and the benzene-1,4-dicarboxylate moiety lies on inversion center. The water O atom occupies the apical position and the basal plane is occupied by two O atoms and two N atoms. Each benzene-1,4- dicarboxylate anion acts as a bis-monodentate ligand that binds two Cu^II cations, forming an infinite chain extending parallel to [001] (Fig. 2). The N⁶-benzyladenine ligands are attached on both sides of the chain. The neighbouring chains are connected into two dimensional layers via O—H···O and N—H···O hydrogen bonds, and the adjacent layers are further packed via N—H···N hydrogen bonds into the three dimensional supramolecular architecture (Table 1, Fig. 3).

Related literature top

For examples of the use of biomolecules in metal-organic frameworks, see: An et al. (2009); Lee et al. (2008); Xie et al. (2007).

Experimental top

A mixture of benzene-1,4-dicarboxylate acid (0.017 g, 0.1 mmol), N⁶-benzyladenine (0.023 g, 0.1 mmol), and Cu(NO₃)₂.3H₂O (0.024 g, 0.1 mmol) in H₂O (10.0 ml) was placed in a 16 ml Teflon-lined stainless steel vessel and heated to 120 °C for 72 h, then cooled to room temperature at a rate of -5 °C/h. Afer filtration, dark blue block crystals are obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot of (I) at the 50% probability level. H atoms are represented by circles of arbitrary size. Symmetry code: (i)-x + 1, -y, -z + 1; (ii)-x + 1, y, -z + 1/2.
	Fig. 2. The one-dimensional chain structure of (I). Non-associative H atoms are omitted.
	Fig. 3. The packing diagram of (I) showing hydrogen bonding interactions (light blue dashed lines).

catena-Poly[[aquabis(N⁶-benzyladenine- κN³)copper(II)]-µ-benzene-1,4-dicarboxylato- κ²O¹:O⁴] top

Crystal data top

[Cu(C₈H₄O₄)(C₁₂H₁₁N₅)₂(H₂O)]	F(000) = 1436
M_r = 696.18	D_x = 1.486 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.171 (2) Å	Cell parameters from 3162 reflections
b = 5.554 (1) Å	θ = 3.0–27.3°
c = 22.102 (1) Å	µ = 0.76 mm⁻¹
β = 115.868 (1)°	T = 296 K
V = 3111.6 (6) Å³	Block, blue
Z = 4	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2744 independent reflections
Radiation source: fine-focus sealed tube	2455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −30→33
T_min = 0.884, T_max = 0.897	k = −6→6
7556 measured reflections	l = −25→26

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0245P)² + 4.4543P] where P = (F_o² + 2F_c²)/3
2744 reflections	(Δ/σ)_max = 0.012
218 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₈H₄O₄)(C₁₂H₁₁N₅)₂(H₂O)]	V = 3111.6 (6) Å³
M_r = 696.18	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.171 (2) Å	µ = 0.76 mm⁻¹
b = 5.554 (1) Å	T = 296 K
c = 22.102 (1) Å	0.17 × 0.15 × 0.15 mm
β = 115.868 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2744 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2455 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.897	R_int = 0.026
7556 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
2744 reflections	Δρ_min = −0.31 e Å⁻³
218 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
C1	0.21656 (11)	−0.0279 (5)	0.16879 (14)	0.0529 (7)
H1	0.2405	0.0865	0.1682	0.063*
C2	0.19178 (13)	0.0055 (6)	0.21029 (16)	0.0680 (9)
H2	0.1992	0.1421	0.2372	0.082*
C3	0.15662 (13)	−0.1605 (7)	0.21196 (17)	0.0706 (9)
H3	0.1402	−0.1381	0.2400	0.085*
C4	0.14592 (12)	−0.3596 (7)	0.17203 (17)	0.0688 (9)
H4	0.1221	−0.4737	0.1731	0.083*
C5	0.17008 (10)	−0.3938 (5)	0.12996 (14)	0.0533 (7)
H5	0.1620	−0.5292	0.1025	0.064*
C6	0.20617 (8)	−0.2284 (4)	0.12849 (11)	0.0375 (5)
C7	0.23445 (9)	−0.2828 (4)	0.08544 (12)	0.0398 (6)
H7A	0.2598	−0.4101	0.1070	0.048*
H7B	0.2088	−0.3439	0.0424	0.048*
C8	0.31312 (8)	−0.0374 (4)	0.10970 (10)	0.0305 (5)
C9	0.34020 (8)	0.1452 (4)	0.09326 (10)	0.0302 (5)
C10	0.36693 (9)	0.4238 (5)	0.05042 (11)	0.0424 (6)
H10	0.3680	0.5461	0.0223	0.051*
C11	0.39354 (8)	0.1695 (4)	0.13382 (9)	0.0264 (5)
C12	0.39179 (8)	−0.1299 (4)	0.20000 (10)	0.0301 (5)
H12	0.4091	−0.2269	0.2376	0.036*
C13	0.49770 (7)	−0.0984 (4)	0.37039 (9)	0.0243 (4)
C14	0.49924 (8)	−0.0458 (4)	0.43782 (9)	0.0249 (4)
C15	0.48078 (9)	0.1719 (4)	0.44969 (10)	0.0321 (5)
H15	0.4679	0.2879	0.4160	0.039*
C16	0.48156 (9)	0.2161 (4)	0.51161 (10)	0.0331 (5)
H16	0.4690	0.3622	0.5194	0.040*
Cu1	0.5000	0.07414 (6)	0.2500	0.01886 (11)
N5	0.42174 (6)	0.0364 (3)	0.18941 (8)	0.0254 (4)
N6	0.41010 (7)	0.3488 (3)	0.10540 (8)	0.0344 (4)
H6	0.4407	0.4096	0.1204	0.041*
N7	0.32360 (7)	0.3089 (4)	0.04042 (9)	0.0402 (5)
N8	0.26185 (7)	−0.0814 (4)	0.07311 (9)	0.0393 (5)
H8	0.2441	0.0147	0.0405	0.047*
N9	0.34090 (7)	−0.1755 (3)	0.16430 (9)	0.0326 (4)
O1	0.48680 (5)	0.0769 (3)	0.32972 (6)	0.0249 (3)
O2	0.50664 (7)	−0.3073 (3)	0.35810 (7)	0.0418 (4)
O1W	0.5000	0.4643 (4)	0.2500	0.0417 (6)
H1W	0.4975	0.5551	0.2799	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0511 (16)	0.0493 (17)	0.0595 (17)	−0.0067 (13)	0.0253 (14)	−0.0023 (14)
C2	0.079 (2)	0.067 (2)	0.0635 (19)	0.0095 (18)	0.0359 (17)	−0.0076 (16)
C3	0.071 (2)	0.089 (3)	0.069 (2)	0.0161 (19)	0.0456 (18)	0.0113 (19)
C4	0.0547 (18)	0.085 (2)	0.080 (2)	−0.0095 (17)	0.0410 (17)	0.0169 (19)
C5	0.0473 (15)	0.0555 (18)	0.0581 (17)	−0.0127 (13)	0.0238 (13)	0.0005 (14)
C6	0.0275 (11)	0.0427 (14)	0.0368 (12)	−0.0031 (10)	0.0090 (10)	0.0071 (11)
C7	0.0284 (11)	0.0450 (15)	0.0417 (13)	−0.0087 (11)	0.0113 (10)	−0.0022 (11)
C8	0.0247 (10)	0.0400 (13)	0.0259 (11)	−0.0013 (10)	0.0102 (9)	0.0007 (10)
C9	0.0254 (11)	0.0389 (13)	0.0231 (10)	−0.0004 (9)	0.0077 (9)	0.0044 (9)
C10	0.0345 (12)	0.0519 (15)	0.0331 (12)	−0.0023 (12)	0.0077 (10)	0.0198 (12)
C11	0.0234 (10)	0.0356 (12)	0.0189 (10)	−0.0008 (9)	0.0081 (8)	0.0010 (9)
C12	0.0277 (11)	0.0390 (13)	0.0227 (10)	0.0022 (9)	0.0100 (9)	0.0069 (9)
C13	0.0257 (10)	0.0324 (12)	0.0162 (9)	0.0004 (9)	0.0105 (8)	−0.0013 (9)
C14	0.0355 (11)	0.0261 (11)	0.0168 (9)	0.0004 (9)	0.0148 (8)	−0.0002 (8)
C15	0.0530 (14)	0.0271 (11)	0.0196 (10)	0.0082 (10)	0.0190 (10)	0.0065 (9)
C16	0.0564 (14)	0.0246 (11)	0.0254 (11)	0.0086 (10)	0.0244 (10)	0.0015 (9)
Cu1	0.02049 (18)	0.02546 (19)	0.01114 (16)	0.000	0.00736 (13)	0.000
N5	0.0219 (8)	0.0360 (10)	0.0180 (8)	−0.0006 (8)	0.0085 (7)	0.0026 (7)
N6	0.0238 (9)	0.0454 (12)	0.0270 (9)	−0.0074 (8)	0.0047 (8)	0.0096 (8)
N7	0.0292 (10)	0.0512 (13)	0.0321 (10)	−0.0013 (9)	0.0058 (8)	0.0160 (9)
N8	0.0237 (9)	0.0524 (13)	0.0346 (10)	−0.0063 (9)	0.0060 (8)	0.0112 (10)
N9	0.0255 (9)	0.0416 (11)	0.0288 (10)	−0.0026 (8)	0.0100 (8)	0.0075 (8)
O1	0.0310 (7)	0.0314 (8)	0.0161 (6)	0.0058 (6)	0.0138 (6)	0.0044 (6)
O2	0.0755 (12)	0.0309 (9)	0.0264 (8)	0.0113 (8)	0.0291 (8)	−0.0011 (7)
O1W	0.0846 (18)	0.0243 (12)	0.0234 (11)	0.000	0.0305 (12)	0.000

Geometric parameters (Å, º) top

C1—C6	1.375 (4)	C11—N5	1.355 (2)
C1—C2	1.386 (4)	C11—N6	1.364 (3)
C1—H1	0.9300	C12—N9	1.325 (3)
C2—C3	1.366 (4)	C12—N5	1.339 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.364 (5)	C13—O2	1.242 (2)
C3—H3	0.9300	C13—O1	1.269 (2)
C4—C5	1.384 (4)	C13—C14	1.501 (2)
C4—H4	0.9300	C14—C16ⁱ	1.382 (3)
C5—C6	1.381 (3)	C14—C15	1.386 (3)
C5—H5	0.9300	C15—C16	1.381 (3)
C6—C7	1.514 (3)	C15—H15	0.9300
C7—N8	1.451 (3)	C16—C14ⁱ	1.382 (3)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	Cu1—O1ⁱⁱ	1.9531 (12)
C8—N8	1.334 (3)	Cu1—O1	1.9531 (12)
C8—N9	1.354 (3)	Cu1—N5ⁱⁱ	2.0301 (16)
C8—C9	1.409 (3)	Cu1—N5	2.0301 (15)
C9—C11	1.380 (3)	Cu1—O1W	2.167 (2)
C9—N7	1.390 (3)	N6—H6	0.8474
C10—N7	1.308 (3)	N8—H8	0.8600
C10—N6	1.356 (3)	O1W—H1W	0.8593
C10—H10	0.9300

C6—C1—C2	120.7 (3)	N9—C12—H12	115.5
C6—C1—H1	119.6	N5—C12—H12	115.5
C2—C1—H1	119.6	O2—C13—O1	124.85 (17)
C3—C2—C1	120.5 (3)	O2—C13—C14	118.56 (18)
C3—C2—H2	119.7	O1—C13—C14	116.59 (18)
C1—C2—H2	119.7	C16ⁱ—C14—C15	119.42 (17)
C2—C3—C4	119.2 (3)	C16ⁱ—C14—C13	120.10 (18)
C2—C3—H3	120.4	C15—C14—C13	120.47 (18)
C4—C3—H3	120.4	C16—C15—C14	119.85 (19)
C3—C4—C5	120.8 (3)	C16—C15—H15	120.1
C3—C4—H4	119.6	C14—C15—H15	120.1
C5—C4—H4	119.6	C15—C16—C14ⁱ	120.73 (19)
C6—C5—C4	120.5 (3)	C15—C16—H16	119.6
C6—C5—H5	119.8	C14ⁱ—C16—H16	119.6
C4—C5—H5	119.8	O1ⁱⁱ—Cu1—O1	179.10 (9)
C1—C6—C5	118.3 (2)	O1ⁱⁱ—Cu1—N5ⁱⁱ	90.94 (6)
C1—C6—C7	123.2 (2)	O1—Cu1—N5ⁱⁱ	89.15 (6)
C5—C6—C7	118.5 (2)	O1ⁱⁱ—Cu1—N5	89.15 (6)
N8—C7—C6	115.7 (2)	O1—Cu1—N5	90.94 (6)
N8—C7—H7A	108.4	N5ⁱⁱ—Cu1—N5	168.16 (10)
C6—C7—H7A	108.4	O1ⁱⁱ—Cu1—O1W	89.55 (4)
N8—C7—H7B	108.4	O1—Cu1—O1W	89.55 (4)
C6—C7—H7B	108.4	N5ⁱⁱ—Cu1—O1W	95.92 (5)
H7A—C7—H7B	107.4	N5—Cu1—O1W	95.92 (5)
N8—C8—N9	119.24 (19)	C12—N5—C11	111.72 (16)
N8—C8—C9	122.70 (19)	C12—N5—Cu1	122.80 (13)
N9—C8—C9	118.05 (18)	C11—N5—Cu1	125.48 (13)
C11—C9—N7	110.70 (18)	C10—N6—C11	106.49 (17)
C11—C9—C8	117.49 (19)	C10—N6—H6	126.1
N7—C9—C8	131.77 (19)	C11—N6—H6	127.2
N7—C10—N6	114.0 (2)	C10—N7—C9	103.31 (17)
N7—C10—H10	123.0	C8—N8—C7	123.45 (19)
N6—C10—H10	123.0	C8—N8—H8	118.3
N5—C11—N6	129.28 (18)	C7—N8—H8	118.3
N5—C11—C9	125.26 (19)	C12—N9—C8	118.51 (18)
N6—C11—C9	105.46 (17)	C13—O1—Cu1	123.41 (12)
N9—C12—N5	128.93 (19)	Cu1—O1W—H1W	126.0

C6—C1—C2—C3	0.1 (5)	N6—C11—N5—Cu1	1.5 (3)
C1—C2—C3—C4	−0.3 (5)	C9—C11—N5—Cu1	−179.13 (16)
C2—C3—C4—C5	−0.3 (5)	O1ⁱⁱ—Cu1—N5—C12	131.20 (16)
C3—C4—C5—C6	1.1 (5)	O1—Cu1—N5—C12	−49.70 (16)
C2—C1—C6—C5	0.7 (4)	N5ⁱⁱ—Cu1—N5—C12	40.65 (16)
C2—C1—C6—C7	−176.0 (3)	O1W—Cu1—N5—C12	−139.35 (16)
C4—C5—C6—C1	−1.2 (4)	O1ⁱⁱ—Cu1—N5—C11	−47.81 (16)
C4—C5—C6—C7	175.6 (2)	O1—Cu1—N5—C11	131.29 (16)
C1—C6—C7—N8	−17.5 (3)	N5ⁱⁱ—Cu1—N5—C11	−138.35 (16)
C5—C6—C7—N8	165.8 (2)	O1W—Cu1—N5—C11	41.65 (16)
N8—C8—C9—C11	−178.2 (2)	N7—C10—N6—C11	0.0 (3)
N9—C8—C9—C11	0.5 (3)	N5—C11—N6—C10	179.7 (2)
N8—C8—C9—N7	−0.9 (4)	C9—C11—N6—C10	0.3 (2)
N9—C8—C9—N7	177.8 (2)	N6—C10—N7—C9	−0.2 (3)
N7—C9—C11—N5	−179.9 (2)	C11—C9—N7—C10	0.4 (3)
C8—C9—C11—N5	−2.1 (3)	C8—C9—N7—C10	−177.0 (2)
N7—C9—C11—N6	−0.4 (2)	N9—C8—N8—C7	−4.9 (3)
C8—C9—C11—N6	177.40 (19)	C9—C8—N8—C7	173.9 (2)
O2—C13—C14—C16ⁱ	10.3 (3)	C6—C7—N8—C8	95.4 (3)
O1—C13—C14—C16ⁱ	−170.24 (19)	N5—C12—N9—C8	−1.4 (3)
O2—C13—C14—C15	−168.8 (2)	N8—C8—N9—C12	179.8 (2)
O1—C13—C14—C15	10.7 (3)	C9—C8—N9—C12	1.0 (3)
C16ⁱ—C14—C15—C16	−0.2 (4)	O2—C13—O1—Cu1	−16.8 (3)
C13—C14—C15—C16	178.84 (19)	C14—C13—O1—Cu1	163.75 (12)
C14—C15—C16—C14ⁱ	0.2 (4)	O1ⁱⁱ—Cu1—O1—C13	−157.61 (15)
N9—C12—N5—C11	0.0 (3)	N5ⁱⁱ—Cu1—O1—C13	−61.68 (15)
N9—C12—N5—Cu1	−179.12 (17)	N5—Cu1—O1—C13	106.48 (15)
N6—C11—N5—C12	−177.6 (2)	O1W—Cu1—O1—C13	−157.61 (14)
C9—C11—N5—C12	1.8 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱⁱⁱ	0.86	1.80	2.6388 (17)	164
N6—H6···O2^iv	0.85	2.07	2.855 (2)	154
N8—H8···N7^v	0.86	2.20	3.018 (3)	160

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

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₄O₄)(C₁₂H₁₁N₅)₂(H₂O)]
M_r	696.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	28.171 (2), 5.554 (1), 22.102 (1)
β (°)	115.868 (1)
V (Å³)	3111.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.884, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	7556, 2744, 2455
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.03
No. of reflections	2744
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱ	0.86	1.80	2.6388 (17)	164.2
N6—H6···O2ⁱⁱ	0.85	2.07	2.855 (2)	153.9
N8—H8···N7ⁱⁱⁱ	0.86	2.20	3.018 (3)	160.1

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

Acknowledgements

This work was supported financially by the Research Project of Dezhou University (grant No. 07012).

References

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