Aqua[N-(2,5-dihydroxybenzyl)imino­diacetato]copper(II)

Zhang, X.-Q.; Huang, F.-P.; Bian, H.-D.; Yu, Q.; Liang, H.

doi:10.1107/S1600536809042238

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1393

https://doi.org/10.1107/S1600536809042238

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Aqua[N-(2,5-dihydroxybenzyl)iminodiacetato]copper(II)

Xiu-Qing Zhang,^a Fu-Ping Huang,^a He-Dong Bian,^a ^* Qing Yu ^a and Hong Liang ^a

^aKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry and Chemical Engineering of Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: gxnuchem312@yahoo.com.cn

(Received 5 October 2009; accepted 14 October 2009; online 17 October 2009)

The title complex, [Cu(C₁₁H₁₁NO₆)(H₂O)], contains a Cu^II atom in a distorted square-pyramidal geometry. The metal centre is coordinated in the basal sites by one water molecule and two carboxylate O atoms and one N atom of the tetradentate ligand [Cu—O range, 1.9376 (11)–1.9541 (12), Cu—N, 1.9929 (12) Å] while the apical site is occupied by a hydroquinone O donor atom [Cu—O, 2.3746 (12) Å]. Intermolecular hydrogen bonding interactions involving both hydroquinone hydroxy groups and the coordinated water as donors give a three-dimensional framework structure.

Related literature

For general background to p-hydroquinones and their oxidation products p-semiquinones and p-quinones, see: Dooley et al. (1998 ); Wang et al. (1996 ); Calvo et al. (2000 ); Iwata et al. (1998 ); Drouza et al. (2002 ); Huang et al. (2008 ); Addison et al. (1984 ). For the synthesis, see: Fan (1992 ).

Experimental

Crystal data

[Cu(C₁₁H₁₁NO₆)(H₂O)]
M_r = 334.76
Orthorhombic, P b c a
a = 13.0461 (16) Å
b = 9.7919 (12) Å
c = 19.374 (2) Å
V = 2474.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 294 K
0.22 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.693, T_max = 0.813
17710 measured reflections
2929 independent reflections
2662 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.070
S = 1.04
2929 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.76 (3)	1.93 (3)	2.6859 (16)	172 (3)
O6—H4⋯O3ⁱⁱ	0.86 (3)	2.00 (3)	2.8442 (18)	168 (2)
O7—H7A⋯O2ⁱⁱⁱ	0.80 (2)	1.97 (2)	2.7261 (16)	157 (2)
O7—H7B⋯O4^iv	0.87 (3)	1.83 (3)	2.6794 (18)	163 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042238/zs2013sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042238/zs2013Isup2.hkl

checkCIF report

Comment top

p-Hydroquinones, along with their oxidation products p-semiquinones and p-quinones, are very important in the oxidative maintenance of biological amine levels (Dooley et al., 1998), tissue formation (Wang et al., 1996), photosynthesis (Calvo et al., 2000) and aerobic respiration (Iwata et al., 1998). These compounds are involved in interesting organic electron- and hydrogen-transfer systems, e.g. electron-transfer reactions between transition metal centers and p-quinone cofactors are vital for all life (Drouza et al., 2002), occurring in key biological processes. As part of a series of the studies (Huang et al., 2008), we report here the synthesis and structure of the title compound, a new Cu^II complex with the related ligand 2-[N,N-bis(carboxylatomethyl)aminomethyl]hydroquinone. The molecular structure of the title compound [Cu(C₁₁H₁₁NO₆)(H₂O)] (I) is shown in Fig. 1. The Cu^II atom has a distorted square-pyramidal geometry with a τ parameter of 0.09 (Addison et al., 1984). The basal sites are occupied by one water molecule, as well as two carboxylate O atoms and one N atom of the ligand. In the apical position, the O atom of the hydroxybenzene coordinates to the Cu^II atom. All bond distances and bond angles have normal values. The crystal packing of (I) (Fig. 2) involves intermolecular O—H···O hydrogen bonds (Table 1). The non-coordinated carboxylate O2 atom accepts intermolecular hydrogen bonds from the coordinated hydroxy O (O5) of the hydroquinone ligand and from the coordinated water (O7). The non-coordinated carboxylate O4 atom is also an acceptor for a water H donor in an intermolecular hydrogen bond. The coordinated atom O3 accepts a hydrogen bond from the non-coordinated hydroquinone O (O6). These interactions result in a three-dimensional hydrogen-bonded framework structure.

Related literature top

For general background to p-hydroquinones and their oxidation products p-semiquinones and p-quinones, see: Dooley et al. (1998); Wang et al. (1996); Calvo et al. (2000); Iwata et al. (1998); Drouza et al. (2002); Huang et al. (2008); Addison et al. (1984). For the synthesis, see Fan (1992).

Experimental top

The ligand 2-[N,N-bis(carboxylatomethyl)aminomethyl]hydroquinone was prepared according to a literature procedure (Fan et al., 1992). The title complex was synthesized by the addition of CuCl₂.2H₂O (0.0850 g, 0.5 mmol) to 20 ml of a methanol solution containing the ligand (0.1275 g, 0.5 mmol). The resulting solution was stirred for 3 h at 60°C, and then cooled and filtered. Blue single crystal blocks were isolated from the solution at room temperature over six days.

Structure description top

For general background to p-hydroquinones and their oxidation products p-semiquinones and p-quinones, see: Dooley et al. (1998); Wang et al. (1996); Calvo et al. (2000); Iwata et al. (1998); Drouza et al. (2002); Huang et al. (2008); Addison et al. (1984). For the synthesis, see Fan (1992).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

	Fig. 1. A view of the molecular structure of (I) with the atom-numbering scheme and 30% displacement ellipsoids.
	Fig. 2. The packing for (I), showing hydrogen bonds as dashed lines.

Aqua[N-(2,5-dihydroxybenzyl)iminodiacetato]copper(II) top

Crystal data top

[Cu(C₁₁H₁₁NO₆)(H₂O)]	F(000) = 1368
M_r = 334.76	D_x = 1.797 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6907 reflections
a = 13.0461 (16) Å	θ = 1.6–27.9°
b = 9.7919 (12) Å	µ = 1.80 mm⁻¹
c = 19.374 (2) Å	T = 294 K
V = 2474.9 (5) Å³	Block, blue
Z = 8	0.22 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn diffractometer	2929 independent reflections
Radiation source: rotating anode	2662 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.026
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω scans	h = −17→17
Absorption correction: multi-scan (Jacobson, 1998)	k = −12→11
T_min = 0.693, T_max = 0.813	l = −25→22
17710 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 0.7209P] where P = (F_o² + 2F_c²)/3
2929 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₁NO₆)(H₂O)]	V = 2474.9 (5) Å³
M_r = 334.76	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.0461 (16) Å	µ = 1.80 mm⁻¹
b = 9.7919 (12) Å	T = 294 K
c = 19.374 (2) Å	0.22 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn diffractometer	2929 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2662 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.813	R_int = 0.026
17710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
2929 reflections	Δρ_min = −0.56 e Å⁻³
198 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	0.566322 (13)	0.226573 (19)	0.381922 (9)	0.01771 (8)
O1	0.68631 (9)	0.23223 (12)	0.44079 (6)	0.0273 (3)
O2	0.83131 (8)	0.34779 (12)	0.45719 (6)	0.0275 (3)
O3	0.47226 (9)	0.23658 (11)	0.30369 (5)	0.0214 (2)
O4	0.43813 (9)	0.36157 (13)	0.21087 (6)	0.0300 (3)
O5	0.43629 (9)	0.31326 (14)	0.45565 (6)	0.0259 (3)
H5	0.402 (2)	0.269 (3)	0.4779 (13)	0.049 (7)*
O6	0.24306 (11)	0.69678 (15)	0.29249 (7)	0.0402 (3)
H4	0.179 (2)	0.700 (3)	0.3008 (12)	0.046 (6)*
O7	0.54070 (9)	0.03204 (12)	0.39637 (7)	0.0242 (2)
H7A	0.5782 (16)	−0.006 (2)	0.4227 (12)	0.039 (6)*
H7B	0.5424 (18)	−0.010 (3)	0.3566 (13)	0.046 (7)*
N1	0.60886 (9)	0.41382 (12)	0.35356 (6)	0.0164 (2)
C1	0.74866 (11)	0.32885 (16)	0.42719 (7)	0.0205 (3)
C2	0.72035 (11)	0.42214 (16)	0.36733 (8)	0.0225 (3)
H2A	0.7389	0.5155	0.3784	0.027*
H2B	0.7581	0.3952	0.3264	0.027*
C3	0.48912 (11)	0.33842 (16)	0.26298 (7)	0.0200 (3)
C4	0.58171 (11)	0.42657 (17)	0.27948 (7)	0.0209 (3)
H4A	0.6394	0.3983	0.2513	0.025*
H4B	0.5665	0.5212	0.2688	0.025*
C5	0.55454 (11)	0.51871 (16)	0.39631 (8)	0.0212 (3)
H5A	0.5788	0.6087	0.3832	0.025*
H5B	0.5718	0.5046	0.4445	0.025*
C6	0.44000 (11)	0.51419 (17)	0.38847 (7)	0.0203 (3)
C7	0.38238 (12)	0.41397 (16)	0.42132 (7)	0.0214 (3)
C8	0.27640 (12)	0.41627 (18)	0.41733 (8)	0.0268 (3)
H8	0.2379	0.3530	0.4420	0.032*
C9	0.22764 (13)	0.51300 (19)	0.37651 (8)	0.0288 (4)
H9	0.1565	0.5149	0.3742	0.035*
C10	0.28474 (13)	0.60661 (17)	0.33916 (9)	0.0275 (3)
C11	0.39017 (12)	0.60955 (16)	0.34741 (9)	0.0268 (3)
H11	0.4282	0.6766	0.3251	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01778 (12)	0.01416 (12)	0.02119 (11)	−0.00129 (6)	−0.00341 (6)	0.00288 (6)
O1	0.0249 (6)	0.0251 (6)	0.0320 (6)	−0.0065 (5)	−0.0100 (5)	0.0112 (4)
O2	0.0206 (5)	0.0312 (6)	0.0306 (6)	−0.0049 (5)	−0.0093 (4)	0.0097 (5)
O3	0.0218 (5)	0.0199 (5)	0.0226 (5)	−0.0030 (4)	−0.0037 (4)	0.0019 (4)
O4	0.0303 (6)	0.0343 (7)	0.0254 (6)	−0.0017 (5)	−0.0107 (4)	0.0048 (5)
O5	0.0266 (6)	0.0260 (6)	0.0251 (6)	0.0021 (5)	0.0062 (4)	0.0086 (5)
O6	0.0264 (7)	0.0411 (8)	0.0532 (8)	0.0104 (6)	−0.0013 (6)	0.0175 (6)
O7	0.0251 (5)	0.0158 (5)	0.0317 (6)	−0.0001 (5)	−0.0054 (5)	0.0033 (5)
N1	0.0135 (5)	0.0169 (6)	0.0187 (5)	0.0001 (4)	−0.0009 (4)	0.0026 (4)
C1	0.0194 (6)	0.0198 (7)	0.0223 (6)	0.0012 (6)	−0.0013 (5)	0.0025 (5)
C2	0.0150 (6)	0.0240 (7)	0.0285 (7)	−0.0019 (6)	−0.0034 (5)	0.0084 (6)
C3	0.0190 (7)	0.0212 (7)	0.0200 (7)	0.0024 (5)	0.0003 (5)	−0.0017 (5)
C4	0.0200 (7)	0.0239 (8)	0.0188 (7)	−0.0013 (6)	−0.0007 (5)	0.0054 (5)
C5	0.0212 (7)	0.0156 (7)	0.0266 (7)	−0.0005 (5)	−0.0002 (6)	−0.0034 (6)
C6	0.0199 (7)	0.0172 (7)	0.0236 (7)	0.0014 (5)	0.0027 (5)	−0.0022 (5)
C7	0.0248 (7)	0.0207 (7)	0.0186 (6)	0.0031 (6)	0.0041 (5)	−0.0009 (5)
C8	0.0231 (7)	0.0309 (9)	0.0263 (8)	−0.0033 (7)	0.0063 (6)	0.0022 (6)
C9	0.0190 (7)	0.0348 (9)	0.0327 (8)	0.0027 (7)	0.0036 (6)	−0.0010 (6)
C10	0.0250 (8)	0.0245 (8)	0.0329 (8)	0.0074 (6)	0.0014 (6)	0.0016 (6)
C11	0.0239 (8)	0.0201 (8)	0.0363 (8)	0.0020 (6)	0.0049 (6)	0.0059 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.9376 (11)	C1—C2	1.522 (2)
Cu1—O3	1.9526 (11)	C2—H2A	0.9700
Cu1—O7	1.9541 (12)	C2—H2B	0.9700
Cu1—N1	1.9929 (12)	C3—C4	1.519 (2)
Cu1—O5	2.3746 (12)	C4—H4A	0.9700
O1—C1	1.2752 (19)	C4—H4B	0.9700
O2—C1	1.2390 (18)	C5—C6	1.503 (2)
O3—C3	1.2903 (18)	C5—H5A	0.9700
O4—C3	1.2302 (18)	C5—H5B	0.9700
O5—C7	1.3818 (19)	C6—C11	1.388 (2)
O5—H5	0.76 (3)	C6—C7	1.390 (2)
O6—C10	1.376 (2)	C7—C8	1.385 (2)
O6—H4	0.86 (3)	C8—C9	1.388 (2)
O7—H7A	0.80 (2)	C8—H8	0.9300
O7—H7B	0.87 (3)	C9—C10	1.385 (2)
N1—C2	1.4810 (18)	C9—H9	0.9300
N1—C4	1.4834 (17)	C10—C11	1.385 (2)
N1—C5	1.4976 (19)	C11—H11	0.9300

O1—Cu1—O3	164.41 (5)	O4—C3—O3	123.49 (14)
O1—Cu1—O7	94.69 (5)	O4—C3—C4	119.88 (14)
O3—Cu1—O7	93.01 (5)	O3—C3—C4	116.50 (12)
O1—Cu1—N1	84.90 (5)	N1—C4—C3	110.22 (11)
O3—Cu1—N1	85.11 (5)	N1—C4—H4A	109.6
O7—Cu1—N1	169.72 (5)	C3—C4—H4A	109.6
O1—Cu1—O5	102.29 (5)	N1—C4—H4B	109.6
O3—Cu1—O5	90.00 (5)	C3—C4—H4B	109.6
O7—Cu1—O5	98.05 (5)	H4A—C4—H4B	108.1
N1—Cu1—O5	92.06 (5)	N1—C5—C6	113.23 (12)
C1—O1—Cu1	114.51 (9)	N1—C5—H5A	108.9
C3—O3—Cu1	113.96 (9)	C6—C5—H5A	108.9
C7—O5—Cu1	109.22 (9)	N1—C5—H5B	108.9
C7—O5—H5	112 (2)	C6—C5—H5B	108.9
Cu1—O5—H5	124 (2)	H5A—C5—H5B	107.7
C10—O6—H4	106.8 (16)	C11—C6—C7	118.94 (14)
Cu1—O7—H7A	116.0 (17)	C11—C6—C5	120.25 (14)
Cu1—O7—H7B	109.1 (17)	C7—C6—C5	120.81 (14)
H7A—O7—H7B	109 (2)	O5—C7—C8	123.13 (14)
C2—N1—C4	113.83 (11)	O5—C7—C6	116.67 (13)
C2—N1—C5	109.11 (11)	C8—C7—C6	120.18 (14)
C4—N1—C5	111.37 (11)	C7—C8—C9	120.03 (15)
C2—N1—Cu1	105.92 (9)	C7—C8—H8	120.0
C4—N1—Cu1	106.12 (9)	C9—C8—H8	120.0
C5—N1—Cu1	110.28 (9)	C10—C9—C8	120.18 (16)
O2—C1—O1	124.70 (14)	C10—C9—H9	119.9
O2—C1—C2	118.61 (13)	C8—C9—H9	119.9
O1—C1—C2	116.62 (13)	O6—C10—C11	117.07 (15)
N1—C2—C1	110.04 (12)	O6—C10—C9	123.74 (15)
N1—C2—H2A	109.7	C11—C10—C9	119.17 (15)
C1—C2—H2A	109.7	C10—C11—C6	121.15 (15)
N1—C2—H2B	109.7	C10—C11—H11	119.4
C1—C2—H2B	109.7	C6—C11—H11	119.4
H2A—C2—H2B	108.2

O3—Cu1—O1—C1	36.6 (3)	O2—C1—C2—N1	−161.79 (13)
O7—Cu1—O1—C1	155.93 (11)	O1—C1—C2—N1	21.11 (19)
N1—Cu1—O1—C1	−13.76 (11)	Cu1—O3—C3—O4	179.80 (12)
O5—Cu1—O1—C1	−104.76 (11)	Cu1—O3—C3—C4	3.87 (16)
O1—Cu1—O3—C3	−38.9 (2)	C2—N1—C4—C3	145.89 (13)
O7—Cu1—O3—C3	−158.44 (11)	C5—N1—C4—C3	−90.25 (14)
N1—Cu1—O3—C3	11.43 (10)	Cu1—N1—C4—C3	29.79 (13)
O5—Cu1—O3—C3	103.49 (11)	O4—C3—C4—N1	160.38 (13)
O1—Cu1—O5—C7	130.89 (10)	O3—C3—C4—N1	−23.53 (18)
O3—Cu1—O5—C7	−39.44 (10)	C2—N1—C5—C6	−177.33 (12)
O7—Cu1—O5—C7	−132.48 (10)	C4—N1—C5—C6	56.17 (16)
N1—Cu1—O5—C7	45.67 (10)	Cu1—N1—C5—C6	−61.38 (14)
O1—Cu1—N1—C2	23.76 (9)	N1—C5—C6—C11	−102.16 (17)
O3—Cu1—N1—C2	−144.26 (9)	N1—C5—C6—C7	77.03 (17)
O7—Cu1—N1—C2	−64.4 (3)	Cu1—O5—C7—C8	129.74 (13)
O5—Cu1—N1—C2	125.92 (9)	Cu1—O5—C7—C6	−48.69 (15)
O1—Cu1—N1—C4	145.08 (9)	C11—C6—C7—O5	173.46 (14)
O3—Cu1—N1—C4	−22.93 (9)	C5—C6—C7—O5	−5.7 (2)
O7—Cu1—N1—C4	56.9 (3)	C11—C6—C7—C8	−5.0 (2)
O5—Cu1—N1—C4	−112.75 (9)	C5—C6—C7—C8	175.78 (14)
O1—Cu1—N1—C5	−94.17 (9)	O5—C7—C8—C9	−173.82 (15)
O3—Cu1—N1—C5	97.81 (9)	C6—C7—C8—C9	4.6 (2)
O7—Cu1—N1—C5	177.7 (2)	C7—C8—C9—C10	0.6 (3)
O5—Cu1—N1—C5	7.99 (9)	C8—C9—C10—O6	173.45 (16)
Cu1—O1—C1—O2	−177.60 (12)	C8—C9—C10—C11	−5.2 (3)
Cu1—O1—C1—C2	−0.69 (18)	O6—C10—C11—C6	−174.02 (15)
C4—N1—C2—C1	−145.39 (13)	C9—C10—C11—C6	4.7 (3)
C5—N1—C2—C1	89.54 (15)	C7—C6—C11—C10	0.4 (2)
Cu1—N1—C2—C1	−29.17 (14)	C5—C6—C11—C10	179.58 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.76 (3)	1.93 (3)	2.6859 (16)	172 (3)
O6—H4···O3ⁱⁱ	0.86 (3)	2.00 (3)	2.8442 (18)	168 (2)
O7—H7A···O2ⁱⁱⁱ	0.80 (2)	1.97 (2)	2.7261 (16)	157 (2)
O7—H7B···O4^iv	0.87 (3)	1.83 (3)	2.6794 (18)	163 (2)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₁NO₆)(H₂O)]
M_r	334.76
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	13.0461 (16), 9.7919 (12), 19.374 (2)
V (Å³)	2474.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
Crystal size (mm)	0.22 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.693, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	17710, 2929, 2662
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.070, 1.04
No. of reflections	2929
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.56

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.76 (3)	1.93 (3)	2.6859 (16)	172 (3)
O6—H4···O3ⁱⁱ	0.86 (3)	2.00 (3)	2.8442 (18)	168 (2)
O7—H7A···O2ⁱⁱⁱ	0.80 (2)	1.97 (2)	2.7261 (16)	157 (2)
O7—H7B···O4^iv	0.87 (3)	1.83 (3)	2.6794 (18)	163 (2)

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

Acknowledgements

We gratefully acknowledge the Science Foundation of Guangxi (No.0832098, 0731052) and the Teaching and Research Award Programme for Outstanding Young Teachers in Higher Education Institutions of MOE, China.

References

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