Aqua­[4-(hy­droxy­imino­meth­yl)pyridine-κN1](imino­diacetato-κ3O,N,O′)copper(II)

Yang, Y.; Chai, W.; Song, L.; Yang, Y.; Chen, J.

doi:10.1107/S1600536811033459

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1291-m1292

doi:10.1107/S1600536811033459

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Aqua[4-(hydroxyiminomethyl)pyridine-κN¹](iminodiacetato-κ³O,N,O′)copper(II)

Yisheng Yang,^a Wenxiang Chai,^a ^* Li Song,^b Yunyun Yang ^a and Jiongke Chen ^a

^aCollege of Materials Science and Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China, and ^bDepartment of Chemistry, Key Laboratory of Advanced Textile Materials and, Manufacturing Technology of Education Ministry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: wxchai_cm@yahoo.com.cn

(Received 4 August 2011; accepted 17 August 2011; online 27 August 2011)

In the title complex, [Cu(C₄H₅NO₄)(C₆H₆N₂O)(H₂O)], conventionally abbreviated Cu(IDA)(4-OXPy)(H₂O), where IDA is iminodiacetate and 4-OXPy is 4-(hydroxyiminomethyl)pyridine, the Cu^II atom exhibits a distorted square-pyramidal coordination geometry, which is constructed from two O atoms and one N atom from a IDA ligand, one N atom from 4-OXPy ligand and one O atom from water. This molecule looks like a space shuttle, the IDA ligand is its empennage (tail), and the 4-OXPy ligand is its airframe. The complexes are linked into two-dimensional supramolecular layers parallel to (100) by three pairs of O—H⋯O hydrogen bonds. Two pairs of N—H⋯O hydrogen bonds further connect these supramolecular layers, forming a three-dimensional supramolecular network.

Related literature

For related ternary complexes of copper(II), IDA and an N-heterocyclic ligand, see: Roman-Alpiste et al. (1999 ); Kundu et al. (2005 ); Chen et al. (1990 ); Zhang et al. (2008 ); Selvakumar et al. (2006 ); Siddiqi et al. (2009 ); Setha et al. (2010 ); Campos et al. (1996 ); Castineiras et al. (1995 ); Brandi-Blanco et al. (2003 ); Craven et al. (2003 ). For hydrogen bonding, see: Desiraju & Steiner (1999 ). For the PLATON program, see: Spek (2009 ).

Experimental

Crystal data

[Cu(C₄H₅NO₄)(C₆H₆N₂O)(H₂O)]
M_r = 334.78
Triclinic, $[P \overline 1]$
a = 5.520 (7) Å
b = 6.715 (9) Å
c = 17.21 (2) Å
α = 93.41 (2)°
β = 93.952 (13)°
γ = 106.52 (2)°
V = 608.1 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.83 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.838, T_max = 0.838
4742 measured reflections
2739 independent reflections
2269 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.095
S = 1.04
2739 reflections
229 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.82 (2)	1.99 (2)	2.771 (4)	159 (3)
O6—H6A⋯O3ⁱⁱ	0.82 (2)	1.97 (3)	2.694 (4)	147 (3)
O5—H5B⋯O3ⁱⁱⁱ	0.82 (2)	1.99 (2)	2.796 (4)	172 (4)
N1—H1⋯O1^iv	0.83 (3)	2.59 (4)	3.214 (5)	133 (3)
N1—H1⋯O2^iv	0.83 (3)	2.42 (3)	3.026 (4)	130 (3)
Symmetry codes: (i) -x-1, -y-1, -z; (ii) -x-1, -y-1, -z-1; (iii) x-1, y-1, z; (iv) x+1, y, z; (v) -x-3, -y-2, -z-1.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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/S1600536811033459/zk2022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033459/zk2022Isup2.hkl

checkCIF report

Comment top

Due to the tridentate chelating function of the iminodiacetate anion and the plasticity of the copper(ii) coordination stereochemistry, an important research has been devoted to the structure of [Cu(IDA)(H₂)₂]_n (Roman-Alpiste et al., 1999) and a variety of mixed-ligand complexes of copper(ii), IDA and N-heterocyclic donor (auxiliary). These ternary complexes are a source of inorganic structural corelations and bioinorganic model compounds for mono- or di-nuclear copper proteins. Here, we report one of those ternary complexes Cu(IDA)(4-OXPy)(H₂O) (I), composed from copper(ii), IDA and 4-OXPy ligand.

In compound (I), the copper(ii) exhibits distorted square pyramid coordination geometry, which is constructed from two O atoms and one N atom from a IDA ligand, one N atom from 4-OXPy ligand and other one O atom from water. In this CuO₃N₂ square pyramid, the Cu1—O1 = 1.998 (3) Å, Cu1—O4 = 1.969 (3) Å, Cu1—O5 = 2.326 (4) Å, Cu1—N1 = 1.998 (3) Å, Cu1—N2 = 1.968 (3) Å. All bond lengths are within commonly accepted values in the literature (Roman-Alpiste et al., 1999; Kundu et al., 2005; Chen et al., 1990; Zhang et al., 2008). This molecule looks like a space shuttle, the IDA ligand just as its empennage, and the 4-OXPy ligand as its airframe. And by virtue of three pairs of O—H···O and two pairs of N—H···O hydrogen bonds, the complexes are linked into a three-dimensional supramolecular network. The hydrogen bonding data are in the range of standard examples (Desiraju et al., 1999) and have been examined by the PLATON program (Spek, 2009). Firstly, along the crystal plane group of {1 - 1 0}, the adjacent molecules connect each other through three pairs of O—H···O hydrogen bonds [O5—H5A···O2, O5—H5B···O3 and O6—H6A···O3] (details listed in Table 2) to form supramolecular layers. And then, the neighbouring layers fuse one by one via other two pairs of N—H···O hydrogen bonds [N1—H1···O1 and N1—H1···O2] (details listed in Table 2) to give out a 3-D supramolecular network.

Related literature top

For related ternary complexes of copper(II), IDA andan N-heterocyclic ligand, see: Roman-Alpiste et al. (1999); Kundu et al. (2005); Chen et al. (1990); Zhang et al. (2008); Selvakumar et al. (2006); Siddiqi et al. (2009); Setha et al. (2010); Campos et al. (1996); Castineiras et al. (1995); Brandi-Blanco et al. (2003); Craven et al. (2003). For hydrogen bonding, see: Desiraju & Steiner (1999). For the PLATON program, see: Spek (2009);.

Experimental top

The title compound (I) was synthesized by solution reaction of Cu₂(OH)₂CO₃ (23 mg, 0.1 mmol), H₂IDA (27 mg, 0.2 mmol), and 4-AOXPy (25 mg, 0.2 mmol) in 15 ml water at room temperature. The subsequent solution was filtered and placed for evaperation. After several days, the blue crystals of (I) were obtained in a yield of 91% (61 mg). Anal.Calc. for C₁₀H₁₃CuN₃O₆ (%): C, 35.88; H, 3.91; N, 12.55; O, 28.67. Found: C, 35.53; H, 3.66; N, 12.87; O, 28.98. Crystals of (I) suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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. A view of the structure of I, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probabilithy level.
	Fig. 2. The supramolecular organic-inorganic hybrid layer constructed by hydrogen bonds, viewed along the a-direction.
	Fig. 3. The packing diagram of I, viewed along the c-direction.

Aqua[4-(hydroxyiminomethyl)pyridine-κN¹](iminodiacetato- κ³O,N,O')copper(II) top

Crystal data top

[Cu(C₄H₅NO₄)(C₆H₆N₂O)(H₂O)]	V = 608.1 (13) Å³
M_r = 334.78	Z = 2
Triclinic, P1	F(000) = 342
Hall symbol: -P 1	D_x = 1.829 Mg m⁻³
a = 5.520 (7) Å	Mo Kα radiation, λ = 0.71075 Å
b = 6.715 (9) Å	µ = 1.83 mm⁻¹
c = 17.21 (2) Å	T = 293 K
α = 93.41 (2)°	Prism, blue
β = 93.952 (13)°	0.10 × 0.10 × 0.10 mm
γ = 106.52 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2739 independent reflections
Radiation source: fine-focus sealed tube	2269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 14.6306 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
CCD_Profile_fitting scans	h = −6→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→6
T_min = 0.838, T_max = 0.838	l = −22→22
4742 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0435P)²] where P = (F_o² + 2F_c²)/3
2739 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.57 e Å⁻³
3 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Cu(C₄H₅NO₄)(C₆H₆N₂O)(H₂O)]	γ = 106.52 (2)°
M_r = 334.78	V = 608.1 (13) Å³
Triclinic, P1	Z = 2
a = 5.520 (7) Å	Mo Kα radiation
b = 6.715 (9) Å	µ = 1.83 mm⁻¹
c = 17.21 (2) Å	T = 293 K
α = 93.41 (2)°	0.10 × 0.10 × 0.10 mm
β = 93.952 (13)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2739 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2269 reflections with I > 2σ(I)
T_min = 0.838, T_max = 0.838	R_int = 0.036
4742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.57 e Å⁻³
2739 reflections	Δρ_min = −0.50 e Å⁻³
229 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	−0.37748 (7)	−0.42758 (6)	−0.194474 (19)	0.01297 (13)
N1	−0.1348 (5)	−0.2773 (4)	−0.10405 (14)	0.0125 (5)
O1	−0.6388 (4)	−0.4320 (3)	−0.11931 (11)	0.0145 (4)
O2	−0.6897 (4)	−0.3155 (3)	0.00069 (12)	0.0169 (5)
O3	0.2937 (4)	−0.0787 (3)	−0.24552 (12)	0.0178 (5)
O4	−0.0910 (4)	−0.3095 (3)	−0.25623 (11)	0.0154 (5)
O5	−0.3355 (4)	−0.7481 (3)	−0.16195 (12)	0.0165 (5)
N2	−0.6174 (5)	−0.5564 (4)	−0.28578 (13)	0.0113 (5)
C7	−0.9679 (6)	−0.7319 (5)	−0.41322 (16)	0.0146 (6)
O6	−1.3312 (5)	−0.8857 (4)	−0.59936 (13)	0.0241 (5)
C1	−0.5549 (6)	−0.3314 (4)	−0.05274 (16)	0.0133 (6)
C4	0.0914 (6)	−0.1689 (4)	−0.21843 (16)	0.0131 (6)
N3	−1.1134 (5)	−0.7984 (4)	−0.54871 (15)	0.0181 (6)
C3	0.0505 (6)	−0.1025 (5)	−0.13563 (17)	0.0126 (6)
C5	−0.5516 (6)	−0.5396 (5)	−0.35971 (17)	0.0154 (6)
C9	−0.8561 (6)	−0.6636 (5)	−0.27556 (17)	0.0146 (6)
C2	−0.2717 (6)	−0.2199 (5)	−0.03983 (16)	0.0127 (6)
C6	−0.7194 (6)	−0.6254 (5)	−0.42368 (17)	0.0176 (7)
C8	−1.0364 (6)	−0.7541 (5)	−0.33692 (17)	0.0149 (6)
C10	−1.1658 (6)	−0.8162 (5)	−0.47803 (18)	0.0191 (7)
H2B	−0.253 (7)	−0.070 (6)	−0.038 (2)	0.026 (5)*
H9	−0.894 (6)	−0.675 (5)	−0.2254 (19)	0.013 (8)*
H6	−0.668 (7)	−0.608 (6)	−0.475 (2)	0.029 (10)*
H3B	0.201 (7)	−0.051 (6)	−0.102 (2)	0.026 (5)*
H5	−0.393 (7)	−0.473 (5)	−0.3613 (18)	0.012 (8)*
H3A	−0.027 (6)	0.015 (5)	−0.1426 (19)	0.020 (9)*
H8	−1.188 (7)	−0.826 (5)	−0.3240 (19)	0.023 (10)*
H10	−1.331 (7)	−0.874 (5)	−0.4651 (19)	0.023 (9)*
H2A	−0.204 (6)	−0.249 (5)	0.0091 (19)	0.015 (8)*
H1	−0.062 (6)	−0.363 (5)	−0.0895 (19)	0.014 (9)*
H5A	−0.347 (7)	−0.761 (6)	−0.1154 (11)	0.026 (5)*
H5B	−0.439 (6)	−0.853 (4)	−0.1834 (19)	0.026 (5)*
H6A	−1.267 (6)	−0.858 (6)	−0.6405 (14)	0.026 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0110 (2)	0.0155 (2)	0.00976 (18)	0.00041 (15)	−0.00023 (13)	−0.00174 (13)
N1	0.0124 (13)	0.0124 (12)	0.0122 (12)	0.0029 (11)	0.0000 (10)	0.0005 (10)
O1	0.0120 (11)	0.0191 (11)	0.0104 (9)	0.0021 (9)	−0.0006 (8)	−0.0005 (8)
O2	0.0117 (11)	0.0267 (12)	0.0123 (10)	0.0058 (9)	0.0020 (8)	0.0007 (9)
O3	0.0161 (12)	0.0192 (11)	0.0139 (10)	−0.0022 (9)	0.0037 (9)	0.0010 (9)
O4	0.0123 (11)	0.0178 (11)	0.0123 (10)	−0.0011 (9)	0.0006 (8)	−0.0020 (8)
O5	0.0169 (12)	0.0153 (11)	0.0138 (10)	−0.0002 (9)	0.0007 (9)	−0.0006 (9)
N2	0.0088 (12)	0.0129 (12)	0.0115 (11)	0.0025 (10)	−0.0004 (9)	−0.0007 (9)
C7	0.0210 (17)	0.0124 (14)	0.0092 (13)	0.0049 (12)	−0.0040 (12)	−0.0020 (11)
O6	0.0184 (13)	0.0336 (14)	0.0139 (11)	−0.0012 (11)	−0.0008 (9)	−0.0020 (10)
C1	0.0140 (16)	0.0145 (15)	0.0123 (13)	0.0055 (12)	−0.0009 (11)	0.0039 (11)
C4	0.0138 (15)	0.0130 (14)	0.0132 (13)	0.0052 (12)	−0.0003 (11)	0.0018 (11)
N3	0.0179 (14)	0.0198 (14)	0.0161 (12)	0.0074 (11)	−0.0063 (11)	−0.0022 (11)
C3	0.0127 (15)	0.0127 (14)	0.0097 (13)	0.0002 (12)	−0.0002 (11)	−0.0024 (11)
C5	0.0105 (16)	0.0176 (15)	0.0158 (14)	0.0002 (13)	−0.0001 (12)	0.0028 (12)
C9	0.0154 (16)	0.0147 (15)	0.0122 (14)	0.0015 (12)	0.0043 (12)	−0.0005 (11)
C2	0.0123 (15)	0.0134 (15)	0.0108 (13)	0.0021 (12)	0.0012 (11)	−0.0022 (11)
C6	0.0192 (17)	0.0204 (16)	0.0115 (14)	0.0030 (13)	0.0027 (12)	0.0005 (12)
C8	0.0113 (16)	0.0159 (15)	0.0157 (14)	0.0017 (13)	0.0007 (12)	−0.0009 (12)
C10	0.0123 (17)	0.0252 (17)	0.0157 (15)	−0.0002 (14)	0.0005 (12)	−0.0014 (13)

Geometric parameters (Å, º) top

Cu1—N2	1.968 (3)	C7—C10	1.471 (4)
Cu1—O4	1.969 (3)	O6—N3	1.394 (4)
Cu1—O1	1.998 (3)	O6—H6A	0.822 (18)
Cu1—N1	1.998 (3)	C1—C2	1.523 (4)
Cu1—O5	2.326 (4)	C4—C3	1.519 (4)
N1—C2	1.474 (4)	N3—C10	1.274 (4)
N1—C3	1.479 (4)	C3—H3B	0.94 (4)
N1—H1	0.83 (3)	C3—H3A	1.01 (4)
O1—C1	1.281 (4)	C5—C6	1.372 (4)
O2—C1	1.241 (4)	C5—H5	0.87 (3)
O3—C4	1.246 (4)	C9—C8	1.382 (4)
O4—C4	1.274 (4)	C9—H9	0.90 (3)
O5—H5A	0.816 (18)	C2—H2B	0.98 (4)
O5—H5B	0.816 (18)	C2—H2A	0.95 (3)
N2—C9	1.339 (4)	C6—H6	0.95 (4)
N2—C5	1.349 (4)	C8—H8	0.89 (4)
C7—C6	1.385 (5)	C10—H10	0.93 (4)
C7—C8	1.396 (4)

N2—Cu1—O4	94.86 (12)	O3—C4—O4	124.7 (3)
N2—Cu1—O1	96.38 (13)	O3—C4—C3	118.6 (3)
O4—Cu1—O1	158.10 (9)	O4—C4—C3	116.6 (3)
N2—Cu1—N1	175.97 (10)	C10—N3—O6	110.1 (3)
O4—Cu1—N1	83.76 (13)	N1—C3—C4	109.0 (2)
O1—Cu1—N1	83.72 (13)	N1—C3—H3B	112 (2)
N2—Cu1—O5	92.19 (11)	C4—C3—H3B	114 (2)
O4—Cu1—O5	105.52 (10)	N1—C3—H3A	109 (2)
O1—Cu1—O5	92.77 (9)	C4—C3—H3A	103.5 (19)
N1—Cu1—O5	91.83 (11)	H3B—C3—H3A	108 (3)
C2—N1—C3	115.9 (2)	N2—C5—C6	122.7 (3)
C2—N1—Cu1	110.8 (2)	N2—C5—H5	112 (2)
C3—N1—Cu1	106.36 (19)	C6—C5—H5	125 (2)
C2—N1—H1	109 (2)	N2—C9—C8	123.0 (3)
C3—N1—H1	109 (2)	N2—C9—H9	116 (2)
Cu1—N1—H1	105 (2)	C8—C9—H9	121 (2)
C1—O1—Cu1	115.4 (2)	N1—C2—C1	111.4 (2)
C4—O4—Cu1	114.2 (2)	N1—C2—H2B	110 (2)
Cu1—O5—H5A	111 (3)	C1—C2—H2B	107 (2)
Cu1—O5—H5B	117 (3)	N1—C2—H2A	111 (2)
H5A—O5—H5B	104 (4)	C1—C2—H2A	110 (2)
C9—N2—C5	117.8 (3)	H2B—C2—H2A	108 (3)
C9—N2—Cu1	119.8 (2)	C5—C6—C7	119.6 (3)
C5—N2—Cu1	122.4 (2)	C5—C6—H6	121 (2)
C6—C7—C8	118.2 (3)	C7—C6—H6	120 (2)
C6—C7—C10	123.6 (3)	C9—C8—C7	118.7 (3)
C8—C7—C10	118.2 (3)	C9—C8—H8	116 (2)
N3—O6—H6A	97 (3)	C7—C8—H8	125 (2)
O2—C1—O1	124.3 (3)	N3—C10—C7	120.6 (3)
O2—C1—C2	118.4 (3)	N3—C10—H10	122 (2)
O1—C1—C2	117.3 (3)	C7—C10—H10	117 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4	0.87 (3)	2.36 (3)	2.973 (4)	128 (3)
C9—H9···O1	0.90 (3)	2.44 (3)	3.014 (4)	121 (3)
O5—H5A···O2ⁱ	0.82 (2)	1.99 (2)	2.771 (4)	159 (3)
O6—H6A···O3ⁱⁱ	0.82 (2)	1.97 (3)	2.694 (4)	147 (3)
O5—H5B···O3ⁱⁱⁱ	0.82 (2)	1.99 (2)	2.796 (4)	172 (4)
N1—H1···O1^iv	0.83 (3)	2.59 (4)	3.214 (5)	133 (3)
N1—H1···O2^iv	0.83 (3)	2.42 (3)	3.026 (4)	130 (3)
C10—H10···O6^v	0.93 (4)	2.47 (4)	3.340 (5)	156 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₄H₅NO₄)(C₆H₆N₂O)(H₂O)]
M_r	334.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.520 (7), 6.715 (9), 17.21 (2)
α, β, γ (°)	93.41 (2), 93.952 (13), 106.52 (2)
V (Å³)	608.1 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.83
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.838, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	4742, 2739, 2269
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.095, 1.04
No. of reflections	2739
No. of parameters	229
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.50

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4	0.87 (3)	2.36 (3)	2.973 (4)	128 (3)
C9—H9···O1	0.90 (3)	2.44 (3)	3.014 (4)	121 (3)
O5—H5A···O2ⁱ	0.816 (18)	1.99 (2)	2.771 (4)	159 (3)
O6—H6A···O3ⁱⁱ	0.822 (18)	1.97 (3)	2.694 (4)	147 (3)
O5—H5B···O3ⁱⁱⁱ	0.816 (18)	1.986 (19)	2.796 (4)	172 (4)
N1—H1···O1^iv	0.83 (3)	2.59 (4)	3.214 (5)	133 (3)
N1—H1···O2^iv	0.83 (3)	2.42 (3)	3.026 (4)	130 (3)
C10—H10···O6^v	0.93 (4)	2.47 (4)	3.340 (5)	156 (3)

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

Acknowledgements

We are grateful for financial support from the National Natural Science Foundation of China (project 20803070) and the Natural Science Foundation of Zhejiang Province (project Y4100610).

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