Poly[tris­(μ3-5-amino­isophthalato)diaqua­dicerium(III)]

Ma, H.-J.; Fan, Y.-H.; Wang, Q.; Bi, C.-F.; Zhang, D.-M.

doi:10.1107/S160053680803033X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1326

doi:10.1107/S160053680803033X

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Poly[tris(μ₃-5-aminoisophthalato)diaquadicerium(III)]

Hui-Jie Ma,^a Yu-Hua Fan,^a ^* Qiang Wang,^a Cai-Feng Bi ^a and Dong-Mei Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Ocean University of China, Shandong 266100, People's Republic of China
^*Correspondence e-mail: fanyuhua301@163.com

(Received 5 September 2008; accepted 21 September 2008; online 27 September 2008)

In the title complex, [Ce₂(C₈H₅NO₄)₃(H₂O)₂]_n, each Ce ion is in nine-coordinated environment. Eight O atoms from six ligands participate in coordination, in addition to one O atom from a water molecule. Both carboxylate groups from the ligands chelate the Ce atoms, forming two four-membered rings. The 5-aminoisophthalate ligands also bridge the Ce centers, forming a two-dimensional network, and O—H⋯O and N—H⋯O hydrogen bonds complete the structure.

Related literature

For general background, see: Rzaczynska & Belsky (1994 ); Daiguebonne et al. (2000 ); Wu et al. (2002a ,b ); Liao et al. (2004 ).

Experimental

Crystal data

[Ce₂(C₈H₅NO₄)₃(H₂O)₂]
M_r = 853.66
Orthorhombic, P b c n
a = 12.2360 (7) Å
b = 8.0600 (5) Å
c = 25.6700 (15) Å
V = 2531.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 298 (2) K
0.21 × 0.20 × 0.19 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.516, T_max = 0.545 (expected range = 0.474–0.501)
11818 measured reflections
2233 independent reflections
2001 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.045
S = 1.04
2233 reflections
196 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.86	2.63	3.436 (3)	157
N1—H1D⋯O1ⁱⁱ	0.86	2.39	3.154 (3)	148
O1W—H1A⋯O3ⁱ	0.85	2.07	2.898 (3)	165
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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/S160053680803033X/bq2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803033X/bq2095Isup2.hkl

checkCIF report

Comment top

5-aminoisophthalic acid forms covalent bonds with metal ions, especially with transition metals through nitrogen atom of amino group as well as oxygen atoms of carboxylic groups (Wu et al., 2002a; Wu et al., 2002b; Liao et al., 2004) and with lanthanide ions as strong Pearsons acids through oxygen atoms of carboxylic groups (Rzaczynska et al., 1994). Carboxylic groups of acid have a great ability to form infinite connection with metal ions and remarkable versatility in adopting different modes of bonding-from unidendate, chelating and bridging, sometimes in more than one way in the same compound (Daiguebonne et al., 2000). In this paper, we present a title complex, (C₂₄H₁₉Ce₂N₃O₁₄)_n, (I), synthesized by a condensation reaction of 5-aminoisophthalic acid with cerous nitrate under the condition of high pressure.

The molecular structure of the title complex, (I), is shown in Fig.1. The ligands construct a floor-like layer by chelating and bridging metal ions. The carboxy groups link layers in η¹,³ mode, thus resulting in one-dimension metal-channels along b-axis, and the water molecules coordinating with metal ions are pending in these channels.

Related literature top

For general background, see: Rzaczynska et al. (1994); Daiguebonne et al. (2000); Wu et al. (2002a,b); Liao et al. (2004).

Experimental top

5-aminoisophthalic acid (0.3 mmol, 54.6 mg) and sodium hydroxide (0.3 mmol,12.5 mg) dissolved in 20 ml water, heated to boiled and then stop heating. Cerous nitrate hexahydrate (0.3 mmol,130.3 mg) dissolved in 5 ml water was mixed with the above solution, stirring for half an hour. Then transfer them into a 50 ml teflon reactor, under autogenous pressure at 160°C for 3 days and then cooled to room temperature, after which large brown block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Poly[tris(µ₃-5-aminoisophthalato)diaquadicerium(III)] top

Crystal data top

[Ce₂(C₈H₅NO₄)₃(H₂O)₂]	F(000) = 1648
M_r = 853.66	D_x = 2.240 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3043 reflections
a = 12.2360 (7) Å	θ = 2.3–28.4°
b = 8.0600 (5) Å	µ = 3.63 mm⁻¹
c = 25.6700 (15) Å	T = 298 K
V = 2531.6 (3) Å³	Block, brown
Z = 4	0.21 × 0.20 × 0.19 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2233 independent reflections
Radiation source: fine-focus sealed tube	2001 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.516, T_max = 0.545	k = −9→9
11818 measured reflections	l = −30→23

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.045	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0208P)² + 2.5416P] where P = (F_o² + 2F_c²)/3
2233 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.45 e Å⁻³
2 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Ce₂(C₈H₅NO₄)₃(H₂O)₂]	V = 2531.6 (3) Å³
M_r = 853.66	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.2360 (7) Å	µ = 3.63 mm⁻¹
b = 8.0600 (5) Å	T = 298 K
c = 25.6700 (15) Å	0.21 × 0.20 × 0.19 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2233 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2001 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.545	R_int = 0.034
11818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	2 restraints
wR(F²) = 0.045	H-atom parameters constrained
S = 1.04	Δρ_max = 0.45 e Å⁻³
2233 reflections	Δρ_min = −0.64 e Å⁻³
196 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
Ce1	0.694451 (12)	0.038178 (18)	0.094984 (6)	0.01318 (7)
H1A	0.4903	−0.1228	0.0487	0.016*
H1B	0.4671	−0.1140	0.0998	0.016*
N1	0.1463 (2)	0.4699 (3)	0.15158 (11)	0.0302 (7)
H1C	0.1531	0.4128	0.1797	0.036*
H1D	0.1042	0.5534	0.1571	0.036*
N2	0.5000	−0.7310 (4)	0.2500	0.0418 (11)
H2A	0.5462	−0.7843	0.2311	0.050*
O1	0.53914 (15)	0.2297 (2)	0.12641 (8)	0.0227 (5)
O2	0.62001 (17)	0.4491 (3)	0.09148 (8)	0.0250 (5)
O3	0.38087 (15)	0.8402 (2)	−0.01169 (8)	0.0220 (5)
O4	0.77549 (15)	0.2778 (2)	0.03332 (8)	0.0204 (4)
O5	0.63242 (18)	−0.0423 (2)	0.18383 (9)	0.0282 (5)
O6	0.70692 (16)	−0.2648 (2)	0.15024 (8)	0.0232 (5)
O1W	0.51934 (16)	−0.1043 (3)	0.07824 (9)	0.0280 (5)
C1	0.4286 (2)	0.4564 (3)	0.09890 (11)	0.0159 (6)
C2	0.4177 (2)	0.5614 (3)	0.05642 (12)	0.0177 (6)
H2	0.4786	0.5885	0.0365	0.021*
C3	0.3163 (2)	0.6262 (3)	0.04351 (11)	0.0174 (6)
C4	0.2262 (2)	0.5922 (4)	0.07468 (12)	0.0179 (6)
H4	0.1576	0.6316	0.0652	0.021*
C5	0.2384 (2)	0.4998 (3)	0.11991 (12)	0.0189 (6)
C6	0.3393 (2)	0.4281 (3)	0.13138 (12)	0.0182 (6)
H6	0.3469	0.3613	0.1607	0.022*
C7	0.5365 (2)	0.3728 (3)	0.10682 (11)	0.0164 (6)
C8	0.3065 (2)	0.7357 (3)	−0.00284 (12)	0.0173 (6)
C9	0.5727 (2)	−0.2982 (3)	0.21853 (11)	0.0171 (6)
C10	0.5748 (2)	−0.4714 (3)	0.21935 (12)	0.0205 (6)
H10	0.6261	−0.5283	0.1995	0.025*
C11	0.5000	−0.5599 (5)	0.2500	0.0212 (9)
C12	0.5000	−0.2132 (5)	0.2500	0.0176 (9)
H12	0.5000	−0.0978	0.2500	0.021*
C13	0.6425 (2)	−0.1977 (3)	0.18270 (11)	0.0165 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01069 (10)	0.01242 (10)	0.01642 (12)	−0.00009 (6)	−0.00036 (6)	0.00135 (6)
N1	0.0194 (14)	0.0396 (16)	0.0314 (18)	0.0059 (12)	0.0102 (12)	0.0138 (13)
N2	0.070 (3)	0.0152 (19)	0.040 (3)	0.000	0.030 (2)	0.000
O1	0.0200 (10)	0.0169 (10)	0.0311 (13)	0.0053 (8)	0.0002 (9)	0.0026 (9)
O2	0.0132 (11)	0.0306 (12)	0.0314 (14)	−0.0012 (9)	0.0007 (9)	0.0030 (10)
O3	0.0243 (11)	0.0195 (11)	0.0224 (12)	−0.0062 (9)	−0.0041 (9)	0.0065 (9)
O4	0.0179 (10)	0.0227 (11)	0.0205 (11)	−0.0003 (8)	−0.0036 (9)	0.0016 (9)
O5	0.0395 (13)	0.0170 (11)	0.0280 (13)	0.0005 (9)	0.0133 (11)	0.0036 (9)
O6	0.0235 (11)	0.0225 (9)	0.0236 (12)	0.0025 (9)	0.0101 (9)	0.0048 (8)
O1W	0.0187 (11)	0.0323 (12)	0.0329 (13)	−0.0066 (10)	0.0010 (10)	−0.0076 (11)
C1	0.0136 (14)	0.0137 (14)	0.0204 (16)	−0.0002 (11)	−0.0011 (11)	−0.0010 (12)
C2	0.0151 (14)	0.0154 (14)	0.0226 (16)	−0.0004 (11)	0.0026 (13)	−0.0014 (12)
C3	0.0194 (15)	0.0126 (14)	0.0201 (16)	−0.0010 (11)	−0.0020 (12)	−0.0016 (12)
C4	0.0135 (13)	0.0178 (14)	0.0223 (16)	0.0017 (12)	−0.0013 (12)	−0.0024 (13)
C5	0.0140 (14)	0.0195 (14)	0.0233 (17)	0.0003 (12)	0.0011 (13)	0.0001 (13)
C6	0.0155 (14)	0.0168 (14)	0.0225 (17)	0.0002 (11)	−0.0007 (13)	0.0032 (12)
C7	0.0132 (14)	0.0191 (15)	0.0168 (15)	−0.0005 (12)	−0.0013 (12)	−0.0024 (13)
C8	0.0186 (14)	0.0156 (14)	0.0176 (16)	0.0047 (12)	−0.0009 (12)	−0.0033 (12)
C9	0.0185 (14)	0.0173 (14)	0.0155 (15)	−0.0003 (11)	0.0017 (12)	0.0005 (12)
C10	0.0255 (16)	0.0184 (14)	0.0176 (16)	0.0040 (12)	0.0050 (14)	−0.0020 (13)
C11	0.032 (2)	0.015 (2)	0.016 (2)	0.000	0.0031 (19)	0.000
C12	0.021 (2)	0.016 (2)	0.016 (2)	0.000	0.0012 (17)	0.000
C13	0.0162 (14)	0.0189 (14)	0.0144 (15)	−0.0002 (12)	0.0001 (12)	−0.0004 (12)

Geometric parameters (Å, º) top

Ce1—O2ⁱ	2.383 (2)	O6—Ce1ⁱ	2.448 (2)
Ce1—O6ⁱⁱ	2.448 (2)	O1W—H1A	0.8500
Ce1—O1W	2.469 (2)	O1W—H1B	0.8500
Ce1—O5	2.490 (2)	C1—C2	1.387 (4)
Ce1—O3ⁱⁱⁱ	2.5263 (19)	C1—C6	1.393 (4)
Ce1—O1	2.5779 (19)	C1—C7	1.496 (4)
Ce1—O4ⁱ	2.654 (2)	C2—C3	1.387 (4)
Ce1—O4	2.6870 (19)	C2—H2	0.9300
Ce1—O6	2.828 (2)	C3—C4	1.389 (4)
Ce1—C8ⁱⁱⁱ	2.986 (3)	C3—C8	1.486 (4)
N1—C5	1.410 (4)	C4—C5	1.387 (4)
N1—H1C	0.8600	C4—H4	0.9300
N1—H1D	0.8599	C5—C6	1.395 (4)
N2—C11	1.379 (5)	C6—H6	0.9300
N2—H2A	0.8600	C8—O4ⁱⁱⁱ	1.276 (3)
O1—C7	1.258 (3)	C8—Ce1ⁱⁱⁱ	2.986 (3)
O2—C7	1.256 (3)	C9—C12	1.384 (3)
O2—Ce1ⁱⁱ	2.383 (2)	C9—C10	1.396 (4)
O3—C8	1.261 (3)	C9—C13	1.494 (4)
O3—Ce1ⁱⁱⁱ	2.5263 (19)	C10—C11	1.402 (3)
O4—C8ⁱⁱⁱ	1.276 (3)	C10—H10	0.9300
O4—Ce1ⁱⁱ	2.654 (2)	C11—C10^iv	1.402 (3)
O5—C13	1.259 (3)	C12—C9^iv	1.384 (3)
O6—C13	1.268 (3)	C12—H12	0.9300

O2ⁱ—Ce1—O6ⁱⁱ	75.39 (7)	C8ⁱⁱⁱ—O4—Ce1ⁱⁱ	122.81 (17)
O2ⁱ—Ce1—O1W	132.85 (7)	C8ⁱⁱⁱ—O4—Ce1	90.56 (16)
O6ⁱⁱ—Ce1—O1W	146.17 (7)	Ce1ⁱⁱ—O4—Ce1	105.55 (7)
O2ⁱ—Ce1—O5	104.28 (7)	C13—O5—Ce1	102.02 (18)
O6ⁱⁱ—Ce1—O5	77.79 (7)	C13—O6—Ce1ⁱ	164.58 (18)
O1W—Ce1—O5	76.92 (7)	C13—O6—Ce1	85.86 (16)
O2ⁱ—Ce1—O3ⁱⁱⁱ	115.63 (7)	Ce1ⁱ—O6—Ce1	107.23 (7)
O6ⁱⁱ—Ce1—O3ⁱⁱⁱ	114.74 (6)	Ce1—O1W—H1A	126.9
O1W—Ce1—O3ⁱⁱⁱ	73.53 (7)	Ce1—O1W—H1B	125.6
O5—Ce1—O3ⁱⁱⁱ	139.93 (7)	H1A—O1W—H1B	104.5
O2ⁱ—Ce1—O1	153.47 (7)	C2—C1—C6	119.7 (3)
O6ⁱⁱ—Ce1—O1	78.08 (6)	C2—C1—C7	117.8 (3)
O1W—Ce1—O1	72.14 (7)	C6—C1—C7	122.5 (2)
O5—Ce1—O1	69.18 (7)	C3—C2—C1	120.2 (3)
O3ⁱⁱⁱ—Ce1—O1	76.33 (7)	C3—C2—H2	119.9
O2ⁱ—Ce1—O4ⁱ	66.87 (7)	C1—C2—H2	119.9
O6ⁱⁱ—Ce1—O4ⁱ	142.22 (6)	C2—C3—C4	119.9 (3)
O1W—Ce1—O4ⁱ	69.43 (6)	C2—C3—C8	119.1 (2)
O5—Ce1—O4ⁱ	112.50 (6)	C4—C3—C8	121.0 (2)
O3ⁱⁱⁱ—Ce1—O4ⁱ	81.52 (6)	C5—C4—C3	120.2 (3)
O1—Ce1—O4ⁱ	139.66 (6)	C5—C4—H4	119.9
O2ⁱ—Ce1—O4	80.95 (6)	C3—C4—H4	119.9
O6ⁱⁱ—Ce1—O4	72.12 (7)	C4—C5—C6	119.6 (3)
O1W—Ce1—O4	123.51 (7)	C4—C5—N1	119.3 (3)
O5—Ce1—O4	147.09 (6)	C6—C5—N1	121.0 (3)
O3ⁱⁱⁱ—Ce1—O4	49.99 (6)	C1—C6—C5	120.0 (3)
O1—Ce1—O4	91.49 (6)	C1—C6—H6	120.0
O4ⁱ—Ce1—O4	99.54 (6)	C5—C6—H6	120.0
O2ⁱ—Ce1—O6	72.98 (6)	O2—C7—O1	123.6 (3)
O6ⁱⁱ—Ce1—O6	104.06 (7)	O2—C7—C1	117.1 (2)
O1W—Ce1—O6	74.48 (7)	O1—C7—C1	119.3 (2)
O5—Ce1—O6	48.09 (6)	O3—C8—O4ⁱⁱⁱ	120.9 (3)
O3ⁱⁱⁱ—Ce1—O6	141.19 (6)	O3—C8—C3	118.9 (2)
O1—Ce1—O6	113.57 (6)	O4ⁱⁱⁱ—C8—C3	120.2 (2)
O4ⁱ—Ce1—O6	66.99 (6)	O3—C8—Ce1ⁱⁱⁱ	56.79 (15)
O4—Ce1—O6	153.67 (5)	O4ⁱⁱⁱ—C8—Ce1ⁱⁱⁱ	64.13 (15)
O2ⁱ—Ce1—C8ⁱⁱⁱ	99.07 (7)	C3—C8—Ce1ⁱⁱⁱ	175.47 (19)
O6ⁱⁱ—Ce1—C8ⁱⁱⁱ	93.72 (7)	C12—C9—C10	119.9 (3)
O1W—Ce1—C8ⁱⁱⁱ	98.21 (7)	C12—C9—C13	117.3 (3)
O5—Ce1—C8ⁱⁱⁱ	152.07 (7)	C10—C9—C13	122.8 (3)
O3ⁱⁱⁱ—Ce1—C8ⁱⁱⁱ	24.68 (7)	C9—C10—C11	120.4 (3)
O1—Ce1—C8ⁱⁱⁱ	83.09 (7)	C9—C10—H10	119.8
O4ⁱ—Ce1—C8ⁱⁱⁱ	90.61 (7)	C11—C10—H10	119.8
O4—Ce1—C8ⁱⁱⁱ	25.31 (6)	N2—C11—C10^iv	120.60 (18)
O6—Ce1—C8ⁱⁱⁱ	157.60 (7)	N2—C11—C10	120.60 (18)
C5—N1—H1C	119.9	C10^iv—C11—C10	118.8 (4)
C5—N1—H1D	116.1	C9^iv—C12—C9	120.6 (4)
H1C—N1—H1D	109.7	C9^iv—C12—H12	119.7
C11—N2—H2A	120.0	C9—C12—H12	119.7
C7—O1—Ce1	116.27 (17)	O5—C13—O6	120.0 (3)
C7—O2—Ce1ⁱⁱ	155.62 (19)	O5—C13—C9	118.0 (2)
C8—O3—Ce1ⁱⁱⁱ	98.53 (17)	O6—C13—C9	121.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5^v	0.86	2.63	3.436 (3)	157
N1—H1D···O1^vi	0.86	2.39	3.154 (3)	148
O1W—H1A···O3^v	0.85	2.07	2.898 (3)	165

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

Experimental details

Crystal data
Chemical formula	[Ce₂(C₈H₅NO₄)₃(H₂O)₂]
M_r	853.66
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	12.2360 (7), 8.0600 (5), 25.6700 (15)
V (Å³)	2531.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.21 × 0.20 × 0.19

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.516, 0.545
No. of measured, independent and observed [I > 2σ(I)] reflections	11818, 2233, 2001
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.045, 1.04
No. of reflections	2233
No. of parameters	196
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.64

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N2—H2A···O5ⁱ	0.86	2.63	3.436 (3)	156.9
N1—H1D···O1ⁱⁱ	0.86	2.39	3.154 (3)	148.2
O1W—H1A···O3ⁱ	0.85	2.07	2.898 (3)	164.5

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

Acknowledgements

The authors acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, People's Republic of China.

References

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