Diaqua­bis(9-oxo-4,5-diaza­fluoren-3-olato-κ2N4,O3)cadmium(II)

Zhao, Y.-H.; Yuan, X.; Qin, W.-C.; Sheng, L.-X.; Ding, Y.-Z.

doi:10.1107/S1600536807067323

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m266

doi:10.1107/S1600536807067323

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Diaquabis(9-oxo-4,5-diazafluoren-3-olato-κ²N⁴,O³)cadmium(II)

Ya-Hui Zhao,^a Xing Yuan,^a ^* Wei-Chao Qin,^a Lian-Xi Sheng ^a ^* and Yun-Zheng Ding ^a

^aDepartment of Environment Science, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: yuanx@nenu.edu.cn, shenglx@nenu.edu.cn

(Received 22 November 2007; accepted 17 December 2007; online 4 January 2008)

The title compound, [Cd(C₁₁H₅N₂O₂)₂(H₂O)₂], is a mononuclear complex consisting of a Cd^II atom, two 3-hydroxy-4,5-diazafluoren-9-one ligands and two coordinated water molecules. The Cd^II atom, lying on a twofold axis, displays a distorted octahedral coordintion. Adjacent molecules are linked by O—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distance = 3.84 (1) Å], leading to a one-dimensional chain. Weak C—H⋯O hydrogen bonds connect the chains into a two-dimensional supramolecular structure.

Related literature

For related literature, see: Li et al. (2006 ); Rillema et al. (2007 ); Tershansy et al. (2006 ); Zhao et al. (2006 ).

Experimental

Crystal data

[Cd(C₁₁H₅N₂O₂)₂(H₂O)₂]
M_r = 542.77
Monoclinic, C 2/c
a = 28.190 (5) Å
b = 5.572 (4) Å
c = 13.933 (5) Å
β = 110.622 (5)°
V = 2048.3 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 (2) K
0.26 × 0.21 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.760, T_max = 0.833
5972 measured reflections
2406 independent reflections
1965 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.082
S = 1.02
2406 reflections
158 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd1—O1	2.233 (2)
Cd1—N1	2.3217 (19)
Cd1—O2	2.410 (2)

O1—Cd1—O1ⁱ	101.59 (13)
O1—Cd1—N1ⁱ	92.77 (7)
O1—Cd1—N1	105.03 (8)
N1ⁱ—Cd1—N1	151.82 (11)
O1—Cd1—O2	94.62 (9)
O1ⁱ—Cd1—O2	148.19 (7)
N1ⁱ—Cd1—O2	101.27 (7)
N1—Cd1—O2	56.38 (7)
O2—Cd1—O2ⁱ	85.23 (11)
Symmetry code: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2ⁱ	0.82 (2)	2.02 (2)	2.832 (3)	172 (3)
O1—H1B⋯O2ⁱⁱ	0.83 (2)	1.86 (2)	2.686 (3)	170 (4)
C3—H3⋯O3ⁱⁱⁱ	0.93	2.48	3.351 (5)	156
Symmetry codes: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067323/hy2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067323/hy2109Isup2.hkl

checkCIF report

Comment top

The structures of 4,5-diazafluoren-9-one and its metal complexes have been reported (Li et al., 2006; Rillema et al., 2007; Tershansy et al., 2006; Zhao et al., 2006). However, no studies of its derivative, 3-hydroxyl-4,5-diazafluoren-9-one, and any metal complexes of the ligand are known to date. In this paper, we present the crystal structure of the title compound, [Cd(C₁₁H₅N₂O₂)₂(H₂O)₂].

The title compound is a neutral mononuclear complex. The Cd^II atom is six-coordinate and exhibits a distorted octahedral coordintion geometry, defined by two N atoms and two O atoms from two 3-hydroxyl-4,5-diazafluoren-9-one ligands and two O atoms from two aqua ligands (Fig. 1). The Cd—O distances are in the range of 2.233 (2)–2.410 (2)Å and the Cd—N length is 2.322 (2) Å (Table 1). Adjacent molecules are linked by O—H···O hydrogen bonds and π–π interactions [centroid–centroid distance 3.84 (1) Å], leading to a one-dimensional chain. Weak C—H···O hydrogen bonds connect the chains into a two-dimensional supramolecular structure (Fig. 2; Table 2).

Related literature top

For related literature, see: Li et al. (2006); Rillema et al. (2007); Tershansy et al. (2006); Zhao et al. (2006).

Experimental top

Cadmium(II) acetate dihydrate (0.080 g, 0.3 mmol), 3-hydroxyl-4,5-diazafluoren-9-one (0.040 g, 0.2 mmol), sodium hydroxide (0.024 g, 0.4 mmol) and water (14 ml) were placed in a 23 ml Teflon-lined autoclave, which was heated at 423 K for 3 d. After cooling slowly to room temperature at a rate of 10 K h^-1, colorless crystals of the title compound were obtained. Analysis calculated for C₂₂H₁₄CdN₄O₆: C 48.64, H 2.58, N 10.32%; found: C 48.51, H 2.67, N 10.42%.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x + 2, y, -z + 1/2.]
	Fig. 2. A packing diagram for the two-dimensional supramolecular structure via hydrogen bonds (dashed lines).

Diaquabis(9-oxo-4,5-diazafluoren-3-olato- κ²N⁴,O³)cadmium(II) top

Crystal data top

[Cd(C₁₁H₅N₂O₂)₂(H₂O)₂]	F(000) = 1080
M_r = 542.77	D_x = 1.760 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4465 reflections
a = 28.190 (5) Å	θ = 3.0–28.3°
b = 5.572 (4) Å	µ = 1.12 mm⁻¹
c = 13.933 (5) Å	T = 293 K
β = 110.622 (5)°	Block, colorless
V = 2048.3 (17) Å³	0.26 × 0.21 × 0.17 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2406 independent reflections
Radiation source: rotation anode	1965 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 28.3°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −26→37
T_min = 0.760, T_max = 0.833	k = −7→7
5972 measured reflections	l = −18→12

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) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0433P)² + 1.5483P] where P = (F_o² + 2F_c²)/3
2406 reflections	(Δ/σ)_max < 0.001
158 parameters	Δρ_max = 0.62 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cd(C₁₁H₅N₂O₂)₂(H₂O)₂]	V = 2048.3 (17) Å³
M_r = 542.77	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.190 (5) Å	µ = 1.12 mm⁻¹
b = 5.572 (4) Å	T = 293 K
c = 13.933 (5) Å	0.26 × 0.21 × 0.17 mm
β = 110.622 (5)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2406 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1965 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.833	R_int = 0.021
5972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	2 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.62 e Å⁻³
2406 reflections	Δρ_min = −0.36 e Å⁻³
158 parameters

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

	x	y	z	U_iso*/U_eq
Cd1	1.0000	0.24267 (5)	0.2500	0.04153 (11)
N1	0.91692 (7)	0.1412 (4)	0.15373 (15)	0.0337 (4)
N2	0.90481 (8)	0.5376 (4)	−0.00770 (16)	0.0400 (5)
O2	0.95401 (7)	−0.0756 (3)	0.29552 (14)	0.0455 (4)
O3	0.75172 (7)	0.0883 (4)	−0.09790 (15)	0.0553 (5)
C1	0.91486 (9)	−0.0461 (4)	0.21600 (18)	0.0358 (5)
C2	0.87029 (11)	−0.1903 (5)	0.1904 (2)	0.0430 (6)
H2	0.8695	−0.3203	0.2317	0.052*
C3	0.82874 (10)	−0.1395 (5)	0.1061 (2)	0.0423 (6)
H3	0.7995	−0.2322	0.0897	0.051*
C4	0.83130 (9)	0.0555 (5)	0.04508 (18)	0.0366 (5)
C5	0.79449 (9)	0.1567 (5)	−0.0489 (2)	0.0404 (6)
C6	0.82108 (9)	0.3654 (5)	−0.07684 (18)	0.0377 (5)
C7	0.80569 (10)	0.5278 (5)	−0.1560 (2)	0.0470 (6)
H7	0.7731	0.5249	−0.2045	0.056*
C8	0.84113 (12)	0.6963 (5)	−0.1601 (2)	0.0501 (7)
H8	0.8325	0.8102	−0.2122	0.060*
C9	0.88918 (12)	0.6950 (5)	−0.0868 (2)	0.0460 (7)
H9	0.9122	0.8091	−0.0920	0.055*
C10	0.87021 (9)	0.3786 (4)	−0.00494 (17)	0.0334 (5)
C11	0.87612 (9)	0.1865 (4)	0.07194 (19)	0.0327 (5)
O1	0.99406 (8)	0.4960 (4)	0.36946 (16)	0.0505 (5)
H1A	1.0223 (8)	0.519 (6)	0.412 (2)	0.065 (10)*
H1B	0.9809 (13)	0.630 (4)	0.353 (3)	0.067 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02980 (15)	0.03837 (17)	0.04841 (18)	0.000	0.00383 (11)	0.000
N1	0.0281 (10)	0.0314 (10)	0.0377 (11)	−0.0028 (8)	0.0066 (8)	0.0013 (9)
N2	0.0387 (11)	0.0401 (12)	0.0400 (11)	−0.0032 (9)	0.0125 (9)	0.0036 (9)
O2	0.0427 (10)	0.0407 (10)	0.0454 (10)	0.0028 (8)	0.0058 (8)	0.0076 (8)
O3	0.0343 (10)	0.0707 (14)	0.0495 (11)	−0.0142 (9)	0.0005 (8)	−0.0081 (10)
C1	0.0369 (12)	0.0317 (12)	0.0382 (13)	0.0023 (10)	0.0124 (10)	0.0002 (10)
C2	0.0489 (16)	0.0348 (13)	0.0490 (15)	−0.0056 (11)	0.0218 (13)	0.0017 (11)
C3	0.0385 (14)	0.0400 (14)	0.0494 (15)	−0.0123 (11)	0.0168 (12)	−0.0068 (12)
C4	0.0296 (11)	0.0403 (13)	0.0385 (13)	−0.0051 (10)	0.0103 (10)	−0.0061 (11)
C5	0.0331 (13)	0.0464 (14)	0.0396 (13)	−0.0031 (11)	0.0100 (11)	−0.0089 (12)
C6	0.0317 (12)	0.0444 (15)	0.0345 (12)	−0.0003 (10)	0.0085 (10)	−0.0048 (11)
C7	0.0415 (14)	0.0581 (17)	0.0355 (13)	0.0076 (12)	0.0062 (11)	0.0035 (12)
C8	0.0597 (18)	0.0509 (16)	0.0383 (14)	0.0123 (14)	0.0154 (13)	0.0101 (12)
C9	0.0500 (16)	0.0423 (15)	0.0499 (16)	0.0011 (12)	0.0227 (13)	0.0083 (12)
C10	0.0318 (11)	0.0350 (13)	0.0312 (11)	−0.0004 (9)	0.0086 (9)	−0.0022 (10)
C11	0.0296 (12)	0.0320 (12)	0.0353 (12)	−0.0025 (9)	0.0097 (10)	−0.0030 (10)
O1	0.0448 (12)	0.0426 (11)	0.0532 (12)	0.0076 (9)	0.0039 (10)	−0.0025 (10)

Geometric parameters (Å, º) top

Cd1—O1	2.233 (2)	C3—C4	1.397 (4)
Cd1—O1ⁱ	2.233 (2)	C3—H3	0.9300
Cd1—N1ⁱ	2.3217 (19)	C4—C11	1.391 (3)
Cd1—N1	2.3217 (19)	C4—C5	1.468 (4)
Cd1—O2	2.410 (2)	C5—C6	1.507 (4)
Cd1—O2ⁱ	2.410 (2)	C6—C7	1.374 (4)
N1—C11	1.327 (3)	C6—C10	1.396 (3)
N1—C1	1.371 (3)	C7—C8	1.386 (4)
N2—C10	1.328 (3)	C7—H7	0.9300
N2—C9	1.355 (3)	C8—C9	1.380 (4)
O2—C1	1.269 (3)	C8—H8	0.9300
O3—C5	1.219 (3)	C9—H9	0.9300
C1—C2	1.427 (4)	C10—C11	1.482 (4)
C2—C3	1.365 (4)	O1—H1A	0.817 (18)
C2—H2	0.9300	O1—H1B	0.832 (19)

O1—Cd1—O1ⁱ	101.59 (13)	C4—C3—H3	120.9
O1—Cd1—N1ⁱ	92.77 (7)	C11—C4—C3	118.8 (2)
O1ⁱ—Cd1—N1ⁱ	105.03 (8)	C11—C4—C5	109.1 (2)
O1—Cd1—N1	105.03 (8)	C3—C4—C5	132.1 (2)
O1ⁱ—Cd1—N1	92.77 (7)	O3—C5—C4	128.9 (3)
N1ⁱ—Cd1—N1	151.82 (11)	O3—C5—C6	125.5 (3)
O1—Cd1—O2	94.62 (9)	C4—C5—C6	105.5 (2)
O1ⁱ—Cd1—O2	148.19 (7)	C7—C6—C10	119.6 (2)
N1ⁱ—Cd1—O2	101.27 (7)	C7—C6—C5	132.1 (2)
N1—Cd1—O2	56.38 (7)	C10—C6—C5	108.3 (2)
O1—Cd1—O2ⁱ	148.19 (7)	C6—C7—C8	116.8 (2)
O1ⁱ—Cd1—O2ⁱ	94.62 (9)	C6—C7—H7	121.6
N1ⁱ—Cd1—O2ⁱ	56.38 (7)	C8—C7—H7	121.6
N1—Cd1—O2ⁱ	101.27 (7)	C9—C8—C7	120.0 (3)
O2—Cd1—O2ⁱ	85.23 (11)	C9—C8—H8	120.0
C11—N1—C1	118.1 (2)	C7—C8—H8	120.0
C11—N1—Cd1	147.41 (17)	N2—C9—C8	124.0 (3)
C1—N1—Cd1	94.51 (14)	N2—C9—H9	118.0
C10—N2—C9	115.1 (2)	C8—C9—H9	118.0
C1—O2—Cd1	93.31 (15)	N2—C10—C6	124.6 (2)
O2—C1—N1	115.7 (2)	N2—C10—C11	127.3 (2)
O2—C1—C2	124.3 (2)	C6—C10—C11	108.1 (2)
N1—C1—C2	120.0 (2)	N1—C11—C4	124.2 (2)
C3—C2—C1	120.8 (3)	N1—C11—C10	126.9 (2)
C3—C2—H2	119.6	C4—C11—C10	108.9 (2)
C1—C2—H2	119.6	Cd1—O1—H1A	109 (2)
C2—C3—C4	118.2 (2)	Cd1—O1—H1B	120 (2)
C2—C3—H3	120.9	H1A—O1—H1B	107 (3)

O1—Cd1—N1—C11	93.5 (3)	C3—C4—C5—C6	−179.4 (3)
O1ⁱ—Cd1—N1—C11	−9.3 (3)	O3—C5—C6—C7	2.3 (5)
N1ⁱ—Cd1—N1—C11	−139.1 (3)	C4—C5—C6—C7	−179.5 (3)
O2—Cd1—N1—C11	179.0 (3)	O3—C5—C6—C10	−176.9 (3)
O2ⁱ—Cd1—N1—C11	−104.6 (3)	C4—C5—C6—C10	1.4 (3)
O1—Cd1—N1—C1	−87.51 (16)	C10—C6—C7—C8	0.9 (4)
O1ⁱ—Cd1—N1—C1	169.70 (14)	C5—C6—C7—C8	−178.2 (3)
N1ⁱ—Cd1—N1—C1	39.89 (13)	C6—C7—C8—C9	0.1 (4)
O2—Cd1—N1—C1	−2.01 (13)	C10—N2—C9—C8	0.3 (4)
O2ⁱ—Cd1—N1—C1	74.44 (15)	C7—C8—C9—N2	−0.7 (5)
O1—Cd1—O2—C1	107.16 (15)	C9—N2—C10—C6	0.7 (4)
O1ⁱ—Cd1—O2—C1	−13.7 (2)	C9—N2—C10—C11	−179.8 (2)
N1ⁱ—Cd1—O2—C1	−159.08 (14)	C7—C6—C10—N2	−1.3 (4)
N1—Cd1—O2—C1	2.17 (14)	C5—C6—C10—N2	178.0 (2)
O2ⁱ—Cd1—O2—C1	−104.75 (16)	C7—C6—C10—C11	179.0 (2)
Cd1—O2—C1—N1	−3.4 (2)	C5—C6—C10—C11	−1.7 (3)
Cd1—O2—C1—C2	177.7 (2)	C1—N1—C11—C4	−0.2 (4)
C11—N1—C1—O2	−177.1 (2)	Cd1—N1—C11—C4	178.7 (2)
Cd1—N1—C1—O2	3.5 (2)	C1—N1—C11—C10	−180.0 (2)
C11—N1—C1—C2	1.9 (3)	Cd1—N1—C11—C10	−1.1 (5)
Cd1—N1—C1—C2	−177.5 (2)	C3—C4—C11—N1	−1.3 (4)
O2—C1—C2—C3	176.7 (2)	C5—C4—C11—N1	179.7 (2)
N1—C1—C2—C3	−2.2 (4)	C3—C4—C11—C10	178.6 (2)
C1—C2—C3—C4	0.7 (4)	C5—C4—C11—C10	−0.5 (3)
C2—C3—C4—C11	0.9 (4)	N2—C10—C11—N1	1.6 (4)
C2—C3—C4—C5	179.7 (3)	C6—C10—C11—N1	−178.8 (2)
C11—C4—C5—O3	177.7 (3)	N2—C10—C11—C4	−178.3 (2)
C3—C4—C5—O3	−1.2 (5)	C6—C10—C11—C4	1.4 (3)
C11—C4—C5—C6	−0.5 (3)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82 (2)	2.02 (2)	2.832 (3)	172 (3)
O1—H1B···O2ⁱⁱ	0.83 (2)	1.86 (2)	2.686 (3)	170 (4)
C3—H3···O3ⁱⁱⁱ	0.93	2.48	3.351 (5)	156

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₁H₅N₂O₂)₂(H₂O)₂]
M_r	542.77
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.190 (5), 5.572 (4), 13.933 (5)
β (°)	110.622 (5)
V (Å³)	2048.3 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.26 × 0.21 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.760, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	5972, 2406, 1965
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.082, 1.02
No. of reflections	2406
No. of parameters	158
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.36

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Siemens, 1990).

Selected geometric parameters (Å, º) top

Cd1—O1	2.233 (2)	Cd1—O2	2.410 (2)
Cd1—N1	2.3217 (19)

O1—Cd1—O1ⁱ	101.59 (13)	O1ⁱ—Cd1—O2	148.19 (7)
O1—Cd1—N1ⁱ	92.77 (7)	N1ⁱ—Cd1—O2	101.27 (7)
O1—Cd1—N1	105.03 (8)	N1—Cd1—O2	56.38 (7)
N1ⁱ—Cd1—N1	151.82 (11)	O2—Cd1—O2ⁱ	85.23 (11)
O1—Cd1—O2	94.62 (9)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82 (2)	2.02 (2)	2.832 (3)	172 (3)
O1—H1B···O2ⁱⁱ	0.83 (2)	1.86 (2)	2.686 (3)	170 (4)
C3—H3···O3ⁱⁱⁱ	0.93	2.48	3.351 (5)	156

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

Acknowledgements

The authors thank the Key Project of the Chinese Ministry of Education (grant No. 308008) and the Analysis and Testing Foundation of Northeast Normal University for financial support.

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