Di-μ-acetato-κ4O:O-bis­({2-[(piperidin-2-ylmeth­yl)imino­meth­yl]phenolato-κ3N,N′,O}copper(II)) monohydrate

Wang, X.

doi:10.1107/S1600536812023070

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m833

doi:10.1107/S1600536812023070

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Di-μ-acetato-κ⁴O:O-bis({2-[(piperidin-2-ylmethyl)iminomethyl]phenolato-κ³N,N′,O}copper(II)) monohydrate

Xiao-qin Wang ^a ^*

^aDepartment of Medicinal Chemistry and Pharm-analysis, Guangdong Medical College, Dong guan, People's Republic of China
^*Correspondence e-mail: 1545@gdmc.edu.cn

(Received 3 March 2012; accepted 20 May 2012; online 26 May 2012)

In the binuclear centrosymmetric title compound, [Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂]·H₂O, the Cu^II atom is coordinated by two N atoms and one O atom from the Schiff base ligand and an acetate O atom in a distorted suare-planar geometry. The water O atom is invoved in three different hydrogen-bonding interactions, as donor to the acetate O atom and to the the ligand O atom and as acceptor to a ligand N atom.

Related literature

The ligand was prepared according to a literature method, see: Greatti et al. (2008 ).

Experimental

Crystal data

[Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂]·H₂O
M_r = 715.79
Triclinic, $[P \overline 1]$
a = 8.7725 (18) Å
b = 8.8259 (18) Å
c = 11.894 (2) Å
α = 101.98 (3)°
β = 101.04 (3)°
γ = 110.13 (3)°
V = 810.4 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.37 mm⁻¹
T = 292 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.772, T_max = 0.876
7559 measured reflections
3542 independent reflections
2473 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.136
S = 1.24
3542 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W2⋯O2ⁱ	0.79 (6)	2.06 (6)	2.845 (5)	173 (6)
O1W—H1W1⋯O3ⁱⁱ	0.81 (8)	2.24 (9)	2.970 (6)	151 (8)
N2—H1N⋯O1Wⁱⁱⁱ	1.00 (5)	2.09 (5)	3.047 (5)	159 (4)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023070/gw2117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023070/gw2117Isup2.hkl

checkCIF report

Comment top

There are no crystal structure studies of metal complexes of the new tridentate Schiff ligand. In the title compound, the binuclear molecule is centrosymmetric and the copper atom adopts a distorted square geometry, coordinated by N1, N2, O3 from the ligand and O1 from acetate. There are three kinds of hydrogen bonging in O1w of the lattice water with O2 from acetate, O3 and N2 from ligand. Related hydrogen bonding distances are listed in Table 1.

Related literature top

The ligand was prepared according to a literature method, see: Greatti et al. (2008).

Experimental top

0.12 g (1 mmol) of salicylaldehyde and 0.12 g (1 mmol) of 2-(aminomethyl)piperidine were dissolved in 10 ml of methanol. The solution was stirred at room temperature for 1 h and 0.20 g (1 mmol) monohydrate copper(II) acetate was added. The reaction was stirred at room temperature for 30 minutes. The crude product was collected by filtration and then washed with methanol. Blue block shaped crystals suitable for single-crystal X-ray study were obtained by recrystallization from 2:1 MeCN-MeOH solution (5 ml) with the yield of 66%.CH&N elemental analysis. Found (calcd): C, 50.59 (50.29); H, 6.18 (6.15); N, 8.02 (7.82).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂](H₂O), at the 30% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Di-µ-acetato-κ⁴O:O-bis({2-[(piperidin-2- ylmethyl)iminomethyl]phenolato-κ³N,N',O}copper(II)) monohydrate top

Crystal data top

[Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂]·H₂O	Z = 1
M_r = 715.79	F(000) = 374
Triclinic, P1	D_x = 1.467 Mg m⁻³
a = 8.7725 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8259 (18) Å	Cell parameters from 7559 reflections
c = 11.894 (2) Å	θ = 3.4–27.5°
α = 101.98 (3)°	µ = 1.37 mm⁻¹
β = 101.04 (3)°	T = 292 K
γ = 110.13 (3)°	Block, blue
V = 810.4 (3) Å³	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII diffractometer	3542 independent reflections
Radiation source: fine-focus sealed tube	2473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.772, T_max = 0.876	k = −10→11
7559 measured reflections	l = −15→15

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) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.24	w = 1/[σ²(F_o²) + (0.0652P)²] where P = (F_o² + 2F_c²)/3
3542 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

[Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂]·H₂O	γ = 110.13 (3)°
M_r = 715.79	V = 810.4 (3) Å³
Triclinic, P1	Z = 1
a = 8.7725 (18) Å	Mo Kα radiation
b = 8.8259 (18) Å	µ = 1.37 mm⁻¹
c = 11.894 (2) Å	T = 292 K
α = 101.98 (3)°	0.20 × 0.10 × 0.10 mm
β = 101.04 (3)°

Data collection top

Bruker APEXII diffractometer	3542 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2473 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.876	R_int = 0.034
7559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.24	Δρ_max = 0.55 e Å⁻³
3542 reflections	Δρ_min = −0.84 e Å⁻³
211 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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.49939 (5)	0.30738 (5)	1.01386 (3)	0.03597 (17)
O1	0.6331 (3)	0.4839 (3)	0.9559 (2)	0.0377 (5)
O2	0.7691 (4)	0.3218 (3)	0.9094 (3)	0.0531 (7)
O3	0.6639 (3)	0.4046 (3)	1.1697 (2)	0.0440 (6)
N1	0.3578 (4)	0.1242 (4)	1.0631 (2)	0.0376 (6)
N2	0.3251 (4)	0.1769 (4)	0.8508 (2)	0.0401 (7)
C1	0.7429 (5)	0.4504 (4)	0.9107 (3)	0.0381 (7)
C2	0.8387 (6)	0.5763 (5)	0.8546 (4)	0.0541 (10)
H2A	0.9169	0.5389	0.8231	0.081*
H2B	0.9000	0.6844	0.9141	0.081*
H2C	0.7604	0.5858	0.7908	0.081*
C3	0.6383 (5)	0.3757 (4)	1.2699 (3)	0.0411 (8)
C4	0.7613 (6)	0.4822 (5)	1.3792 (3)	0.0554 (10)
H4A	0.8585	0.5680	1.3781	0.066*
C5	0.7393 (7)	0.4609 (6)	1.4868 (4)	0.0724 (14)
H5A	0.8207	0.5344	1.5577	0.087*
C6	0.5978 (7)	0.3316 (7)	1.4920 (4)	0.0782 (15)
H6A	0.5833	0.3192	1.5655	0.094*
C7	0.4810 (7)	0.2237 (6)	1.3877 (3)	0.0645 (12)
H7A	0.3879	0.1348	1.3907	0.077*
C8	0.4966 (5)	0.2425 (5)	1.2753 (3)	0.0457 (9)
C9	0.3696 (5)	0.1199 (4)	1.1711 (3)	0.0407 (8)
H9A	0.2882	0.0287	1.1827	0.049*
C10	0.2178 (5)	−0.0093 (5)	0.9659 (3)	0.0476 (9)
H10A	0.1134	0.0057	0.9662	0.057*
H10B	0.2041	−0.1185	0.9770	0.057*
C11	0.2541 (5)	−0.0029 (4)	0.8480 (3)	0.0444 (8)
H11A	0.3430	−0.0453	0.8431	0.053*
C12	0.1037 (6)	−0.1121 (5)	0.7406 (3)	0.0539 (10)
H12A	0.0094	−0.0806	0.7468	0.065*
H12B	0.0700	−0.2294	0.7394	0.065*
C13	0.1453 (6)	−0.0928 (5)	0.6245 (3)	0.0600 (11)
H13A	0.2260	−0.1421	0.6114	0.072*
H13B	0.0431	−0.1531	0.5578	0.072*
C14	0.2180 (6)	0.0888 (5)	0.6292 (3)	0.0543 (10)
H14A	0.1303	0.1322	0.6285	0.065*
H14B	0.2547	0.0978	0.5580	0.065*
C15	0.3660 (5)	0.1960 (5)	0.7388 (3)	0.0473 (9)
H15A	0.4605	0.1645	0.7332	0.057*
H15B	0.4007	0.3136	0.7409	0.057*
O1W	0.9643 (5)	0.7056 (5)	0.1856 (4)	0.0694 (10)
H1N	0.230 (7)	0.211 (6)	0.859 (4)	0.085 (16)*
H1W1	0.908 (11)	0.625 (10)	0.203 (7)	0.16 (4)*
H1W2	1.033 (8)	0.696 (8)	0.153 (5)	0.10 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0363 (3)	0.0324 (2)	0.0375 (2)	0.00788 (19)	0.01277 (17)	0.01509 (17)
O1	0.0356 (14)	0.0359 (12)	0.0444 (13)	0.0106 (11)	0.0183 (11)	0.0178 (10)
O2	0.0530 (18)	0.0478 (15)	0.0771 (19)	0.0241 (15)	0.0353 (15)	0.0341 (14)
O3	0.0374 (15)	0.0459 (14)	0.0419 (13)	0.0051 (12)	0.0094 (11)	0.0211 (11)
N1	0.0361 (17)	0.0389 (15)	0.0404 (15)	0.0120 (14)	0.0135 (12)	0.0195 (12)
N2	0.0419 (19)	0.0388 (16)	0.0378 (14)	0.0091 (15)	0.0149 (13)	0.0163 (13)
C1	0.032 (2)	0.0364 (18)	0.0431 (17)	0.0094 (16)	0.0105 (15)	0.0143 (15)
C2	0.059 (3)	0.050 (2)	0.069 (2)	0.021 (2)	0.039 (2)	0.032 (2)
C3	0.049 (2)	0.0379 (18)	0.0377 (17)	0.0190 (18)	0.0101 (16)	0.0129 (15)
C4	0.064 (3)	0.043 (2)	0.049 (2)	0.013 (2)	0.010 (2)	0.0138 (18)
C5	0.092 (4)	0.068 (3)	0.037 (2)	0.021 (3)	0.007 (2)	0.005 (2)
C6	0.093 (4)	0.089 (4)	0.038 (2)	0.016 (3)	0.023 (2)	0.021 (2)
C7	0.072 (3)	0.073 (3)	0.045 (2)	0.018 (3)	0.026 (2)	0.023 (2)
C8	0.050 (2)	0.051 (2)	0.0424 (18)	0.023 (2)	0.0174 (17)	0.0175 (17)
C9	0.039 (2)	0.0374 (18)	0.0494 (19)	0.0115 (17)	0.0174 (16)	0.0215 (16)
C10	0.039 (2)	0.0402 (19)	0.050 (2)	−0.0002 (17)	0.0073 (16)	0.0192 (16)
C11	0.043 (2)	0.0354 (18)	0.0478 (19)	0.0063 (17)	0.0102 (16)	0.0166 (15)
C12	0.050 (3)	0.043 (2)	0.052 (2)	0.0030 (19)	0.0039 (18)	0.0180 (18)
C13	0.062 (3)	0.054 (2)	0.048 (2)	0.011 (2)	0.006 (2)	0.0130 (19)
C14	0.063 (3)	0.053 (2)	0.0387 (18)	0.014 (2)	0.0096 (18)	0.0171 (17)
C15	0.053 (3)	0.047 (2)	0.0376 (17)	0.0107 (19)	0.0141 (17)	0.0188 (16)
O1W	0.061 (2)	0.064 (2)	0.091 (3)	0.032 (2)	0.030 (2)	0.0183 (19)

Geometric parameters (Å, º) top

Cu1—O3	1.928 (3)	C6—H6A	0.9300
Cu1—O1	1.944 (2)	C7—C8	1.408 (5)
Cu1—N1	1.946 (3)	C7—H7A	0.9300
Cu1—N2	2.037 (3)	C8—C9	1.426 (5)
O1—C1	1.277 (4)	C9—H9A	0.9300
O2—C1	1.230 (4)	C10—C11	1.504 (5)
O3—C3	1.313 (4)	C10—H10A	0.9700
N1—C9	1.278 (4)	C10—H10B	0.9700
N1—C10	1.459 (5)	C11—C12	1.506 (5)
N2—C15	1.472 (4)	C11—H11A	0.9800
N2—C11	1.482 (4)	C12—C13	1.522 (6)
N2—H1N	1.00 (5)	C12—H12A	0.9700
C1—C2	1.505 (5)	C12—H12B	0.9700
C2—H2A	0.9600	C13—C14	1.491 (6)
C2—H2B	0.9600	C13—H13A	0.9700
C2—H2C	0.9600	C13—H13B	0.9700
C3—C8	1.410 (6)	C14—C15	1.508 (5)
C3—C4	1.412 (5)	C14—H14A	0.9700
C4—C5	1.372 (6)	C14—H14B	0.9700
C4—H4A	0.9300	C15—H15A	0.9700
C5—C6	1.390 (7)	C15—H15B	0.9700
C5—H5A	0.9300	O1W—H1W1	0.81 (8)
C6—C7	1.359 (6)	O1W—H1W2	0.79 (6)

O3—Cu1—O1	91.10 (11)	C7—C8—C9	117.6 (4)
O3—Cu1—N1	91.94 (12)	C3—C8—C9	123.0 (3)
O1—Cu1—N1	176.92 (10)	N1—C9—C8	125.7 (4)
O3—Cu1—N2	173.00 (11)	N1—C9—H9A	117.1
O1—Cu1—N2	93.92 (11)	C8—C9—H9A	117.1
N1—Cu1—N2	83.01 (12)	N1—C10—C11	109.4 (3)
C1—O1—Cu1	114.3 (2)	N1—C10—H10A	109.8
C3—O3—Cu1	126.2 (2)	C11—C10—H10A	109.8
C9—N1—C10	119.3 (3)	N1—C10—H10B	109.8
C9—N1—Cu1	125.8 (3)	C11—C10—H10B	109.8
C10—N1—Cu1	114.6 (2)	H10A—C10—H10B	108.2
C15—N2—C11	111.7 (3)	N2—C11—C10	107.8 (3)
C15—N2—Cu1	121.4 (3)	N2—C11—C12	113.2 (3)
C11—N2—Cu1	106.9 (2)	C10—C11—C12	113.6 (3)
C15—N2—H1N	110 (3)	N2—C11—H11A	107.3
C11—N2—H1N	102 (3)	C10—C11—H11A	107.3
Cu1—N2—H1N	102 (3)	C12—C11—H11A	107.3
O2—C1—O1	123.3 (3)	C11—C12—C13	111.1 (4)
O2—C1—C2	120.4 (3)	C11—C12—H12A	109.4
O1—C1—C2	116.2 (3)	C13—C12—H12A	109.4
C1—C2—H2A	109.5	C11—C12—H12B	109.4
C1—C2—H2B	109.5	C13—C12—H12B	109.4
H2A—C2—H2B	109.5	H12A—C12—H12B	108.0
C1—C2—H2C	109.5	C14—C13—C12	111.0 (3)
H2A—C2—H2C	109.5	C14—C13—H13A	109.4
H2B—C2—H2C	109.5	C12—C13—H13A	109.4
O3—C3—C8	124.0 (3)	C14—C13—H13B	109.4
O3—C3—C4	118.4 (4)	C12—C13—H13B	109.4
C8—C3—C4	117.6 (3)	H13A—C13—H13B	108.0
C5—C4—C3	121.0 (4)	C13—C14—C15	112.9 (3)
C5—C4—H4A	119.5	C13—C14—H14A	109.0
C3—C4—H4A	119.5	C15—C14—H14A	109.0
C4—C5—C6	121.3 (4)	C13—C14—H14B	109.0
C4—C5—H5A	119.4	C15—C14—H14B	109.0
C6—C5—H5A	119.4	H14A—C14—H14B	107.8
C7—C6—C5	118.7 (4)	N2—C15—C14	112.4 (3)
C7—C6—H6A	120.6	N2—C15—H15A	109.1
C5—C6—H6A	120.6	C14—C15—H15A	109.1
C6—C7—C8	122.0 (5)	N2—C15—H15B	109.1
C6—C7—H7A	119.0	C14—C15—H15B	109.1
C8—C7—H7A	119.0	H15A—C15—H15B	107.9
C7—C8—C3	119.4 (4)	H1W1—O1W—H1W2	118 (6)

O3—Cu1—O1—C1	89.0 (2)	C4—C3—C8—C7	1.6 (5)
N2—Cu1—O1—C1	−86.1 (2)	O3—C3—C8—C9	3.1 (6)
O1—Cu1—O3—C3	161.2 (3)	C4—C3—C8—C9	−175.8 (3)
N1—Cu1—O3—C3	−19.3 (3)	C10—N1—C9—C8	−178.6 (3)
O3—Cu1—N1—C9	15.0 (3)	Cu1—N1—C9—C8	−5.0 (5)
N2—Cu1—N1—C9	−169.8 (3)	C7—C8—C9—N1	174.9 (4)
O3—Cu1—N1—C10	−171.1 (3)	C3—C8—C9—N1	−7.7 (6)
N2—Cu1—N1—C10	4.1 (2)	C9—N1—C10—C11	−165.7 (3)
O1—Cu1—N2—C15	22.8 (3)	Cu1—N1—C10—C11	20.0 (4)
N1—Cu1—N2—C15	−157.0 (3)	C15—N2—C11—C10	179.6 (3)
N1—Cu1—N2—C11	−27.3 (2)	Cu1—N2—C11—C10	44.6 (3)
Cu1—O1—C1—O2	−3.8 (4)	C15—N2—C11—C12	−54.0 (5)
Cu1—O1—C1—C2	174.7 (3)	Cu1—N2—C11—C12	171.0 (3)
Cu1—O3—C3—C8	13.7 (5)	N1—C10—C11—N2	−42.4 (4)
Cu1—O3—C3—C4	−167.5 (3)	N1—C10—C11—C12	−168.6 (3)
O3—C3—C4—C5	178.3 (4)	N2—C11—C12—C13	53.5 (5)
C8—C3—C4—C5	−2.8 (6)	C10—C11—C12—C13	176.8 (3)
C3—C4—C5—C6	1.6 (8)	C11—C12—C13—C14	−52.1 (5)
C4—C5—C6—C7	0.9 (8)	C12—C13—C14—C15	52.5 (5)
C5—C6—C7—C8	−2.1 (8)	C11—N2—C15—C14	52.9 (4)
C6—C7—C8—C3	0.8 (7)	Cu1—N2—C15—C14	−179.5 (2)
C6—C7—C8—C9	178.3 (4)	C13—C14—C15—N2	−53.4 (5)
O3—C3—C8—C7	−179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W2···O2ⁱ	0.79 (6)	2.06 (6)	2.845 (5)	173 (6)
O1W—H1W1···O3ⁱⁱ	0.81 (8)	2.24 (9)	2.970 (6)	151 (8)
N2—H1N···O1Wⁱⁱⁱ	1.00 (5)	2.09 (5)	3.047 (5)	159 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₃H₁₇N₂O)₂(C₂H₃O₂)₂]·H₂O
M_r	715.79
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.7725 (18), 8.8259 (18), 11.894 (2)
α, β, γ (°)	101.98 (3), 101.04 (3), 110.13 (3)
V (Å³)	810.4 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.37
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.772, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	7559, 3542, 2473
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.136, 1.24
No. of reflections	3542
No. of parameters	211
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.84

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W2···O2ⁱ	0.79 (6)	2.06 (6)	2.845 (5)	173 (6)
O1W—H1W1···O3ⁱⁱ	0.81 (8)	2.24 (9)	2.970 (6)	151 (8)
N2—H1N···O1Wⁱⁱⁱ	1.00 (5)	2.09 (5)	3.047 (5)	159 (4)

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

Acknowledgements

The author thanks Guangdong Medical college for supporting this study

References

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