Poly[[bis(μ2-4-amino­benzene­sul­fon­ato-κ2N:O)diaqua­manganese(II)] dihydrate]

Li, Z.L.; Xuan, Y.W.; Wu, W.; Xie, D.P.

doi:10.1107/S1600536808025579

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages m1162-m1163

doi:10.1107/S1600536808025579

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Poly[[bis(μ₂-4-aminobenzenesulfonato-κ²N:O)diaquamanganese(II)] dihydrate]

Zhan Ling Li,^a Ya Wen Xuan,^a ^* Wen Wu ^a and Dong Po Xie ^a

^aDepartment of Chemistry, Zhoukou Normal University, Zhoukou 466001, People's Republic of China
^*Correspondence e-mail: bookw@126.com

(Received 27 July 2008; accepted 8 August 2008; online 13 August 2008)

The title compound, {[Mn(NH₂C₆H₄SO₃)₂(H₂O)₂]·2H₂O}_n, was prepared under mild hydrothermal conditions. The unique Mn^II ion is located on a crystallographic inversion center and is coordinated by two –NH₂ and two –SO₃ groups from four 4-aminobenzenesulfonate ligands and by two water molecules in the axial positions, forming a slightly distorted octahedral coordination environment. The 4-aminobenzenesulfonate anions behave as μ₂-bridging ligands to produce a two-dimensional structure. In the crystal structure, intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the layers into a three-dimensional network.

Related literature

For the isostructural Zn and Co compounds, see: Shakeri & Haussuhl (1992 ). For a similar layered structure, see: Cai et al. (2003 ).

Experimental

Crystal data

[Mn(C₆H₆NO₃S)₂(H₂O)₂]·2H₂O
M_r = 471.36
Monoclinic, P 2₁ /n
a = 7.4485 (8) Å
b = 17.4102 (19) Å
c = 7.6509 (9) Å
β = 116.688 (1)°
V = 886.47 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 295 (2) K
0.49 × 0.45 × 0.45 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.547, T_max = 0.625
6604 measured reflections
1637 independent reflections
1585 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.11
1637 reflections
124 parameters
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O4	1.993 (3)
Mn1—N1ⁱ	2.058 (3)
Mn1—O1	2.425 (3)

O4—Mn1—O4ⁱⁱ	180
O4—Mn1—N1ⁱ	92.95 (13)
O4—Mn1—N1ⁱⁱⁱ	87.05 (13)
N1ⁱ—Mn1—N1ⁱⁱⁱ	180
O4—Mn1—O1ⁱⁱ	84.94 (12)
O4—Mn1—O1	95.06 (12)
N1ⁱ—Mn1—O1	86.66 (11)
N1ⁱⁱⁱ—Mn1—O1	93.34 (11)
O1ⁱⁱ—Mn1—O1	180
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2^iv	0.90	2.46	2.980 (4)	117
O5—H3W⋯O1	0.82	2.06	2.855 (5)	164
C2—H2⋯O2	0.93	2.54	2.920 (5)	105
N1—H1B⋯O2ⁱⁱⁱ	0.90	2.41	3.217 (4)	149
O4—H2W⋯O5^v	0.83	1.83	2.651 (5)	175
C2—H2⋯O5^v	0.93	2.53	3.431 (6)	164
O4—H1W⋯O3^vi	0.82	2.02	2.795 (4)	157
N1—H1A⋯O3^vii	0.90	2.24	3.070 (5)	153
C3—H3⋯O3^vii	0.93	2.55	3.300 (5)	138
O5—H4W⋯O2^viii	0.82	2.00	2.815 (5)	175
Symmetry codes: (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) x+1, y, z; (vi) x, y, z-1; (vii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (viii) -x+1, -y+2, -z+2.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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/S1600536808025579/lh2671sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025579/lh2671Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound (I) is illustrated in Fig.1. This consists of one half of Mn^II ion, one 4-aminobenzenesulfonate ligand, one coordinated water molecule and one solvent water molecule. The title compound is isostructural with the Cobalt and Zinc analogs (Shakeri & Haussuhl, 1992). It is interesting to note that the title compound has very similar layered structure as that observed in [Cd(1,5 nds)-(H₂O)₂]_n (Cai et al., 2003) (1,5-nds = 1,5-naphthalenedisulfonate) in which the Cd^II ion is also coordinated octahedrally by two water molecules occupying the axial positions and the layers are connected by hydrogen bonds formed between the coordinated water molecules and the sulfonate O atoms. In the crystal structure of (I) inter-layered hydrogen bonds formed between the coordinated water molecules and the –NH₂ groups with the free –SO₃^- oxygen atoms generate an extended 3-D structure (Fig.2)

Related literature top

For the isostructural Zn and Co compounds, see: Shakeri & Haussuhl (1992). For a similar layered structure, see: Cai et al. (2003).

Experimental top

All the reagents were of AR grade and used without further purification. p-anilinesulfonic acid (0.8690 g, 5 mmol) were dissolved in 50 ml H₂O solution, the mixed solution was basified with 1 mol.L^-1 KOH to pH =7.5. Then the resultant solution was added in 10 ml double-distilled water containing MnCl₂.4H₂O (0.3950 g, 2 mmol), the resulting solution was heated at 423 K for 96 h. After cooling to room temperature, block crystals were obtained in a yield up to 37.6%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 asymmetric unit of the title compound showing 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of the title compound showing hydrogen bonds as dashed lines.

Poly[[bis(µ₂-4-aminobenzenesulfonato-κ²N:O)diaquamanganese(II)] dihydrate] top

Crystal data top

[Mn(C₆H₆NO₃S)₂(H₂O)₂]·2H₂O	F(000) = 486
M_r = 471.36	D_x = 1.766 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2041 reflections
a = 7.4485 (8) Å	θ = 2.5–26.2°
b = 17.4102 (19) Å	µ = 1.04 mm⁻¹
c = 7.6509 (9) Å	T = 295 K
β = 116.688 (1)°	Block, yellow
V = 886.47 (17) Å³	0.49 × 0.45 × 0.45 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1637 independent reflections
Radiation source: fine-focus sealed tube	1585 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 2.3°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −19→20
T_min = 0.547, T_max = 0.625	l = −9→9
6604 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0902P)² + 2.4519P] where P = (F_o² + 2F_c²)/3
1637 reflections	(Δ/σ)_max < 0.001
124 parameters	Δρ_max = 1.19 e Å⁻³
0 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

[Mn(C₆H₆NO₃S)₂(H₂O)₂]·2H₂O	V = 886.47 (17) Å³
M_r = 471.36	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4485 (8) Å	µ = 1.04 mm⁻¹
b = 17.4102 (19) Å	T = 295 K
c = 7.6509 (9) Å	0.49 × 0.45 × 0.45 mm
β = 116.688 (1)°

Data collection top

Bruker SMART CCD diffractometer	1637 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1585 reflections with I > 2σ(I)
T_min = 0.547, T_max = 0.625	R_int = 0.015
6604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.11	Δρ_max = 1.19 e Å⁻³
1637 reflections	Δρ_min = −1.03 e Å⁻³
124 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
Mn1	0.5000	1.0000	0.5000	0.0103 (3)
S1	0.65941 (14)	0.89771 (5)	0.94564 (13)	0.0222 (3)
O1	0.4931 (4)	0.92302 (17)	0.7611 (4)	0.0299 (7)
O2	0.8422 (4)	0.94184 (16)	0.9916 (4)	0.0315 (7)
O3	0.6018 (5)	0.89731 (17)	1.1046 (4)	0.0333 (7)
O4	0.7291 (5)	0.9436 (2)	0.4921 (4)	0.0376 (8)
H1W	0.7114	0.9406	0.3785	0.056*
H2W	0.8495	0.9411	0.5706	0.056*
N1	0.8133 (5)	0.57368 (19)	0.7847 (5)	0.0265 (7)
H1A	0.8601	0.5771	0.6950	0.032*
H1B	0.6918	0.5512	0.7253	0.032*
C1	0.7134 (6)	0.8009 (2)	0.9110 (5)	0.0238 (8)
C2	0.8724 (6)	0.7854 (2)	0.8697 (6)	0.0307 (9)
H2	0.9547	0.8250	0.8669	0.037*
C3	0.9088 (6)	0.7106 (2)	0.8325 (6)	0.0309 (9)
H3	1.0167	0.6997	0.8065	0.037*
C4	0.7828 (6)	0.6515 (2)	0.8344 (5)	0.0236 (8)
C5	0.6261 (6)	0.6673 (2)	0.8804 (6)	0.0289 (9)
H5	0.5452	0.6276	0.8857	0.035*
C6	0.5900 (6)	0.7421 (2)	0.9184 (6)	0.0288 (9)
H6	0.4847	0.7529	0.9485	0.035*
O5	0.1093 (5)	0.9329 (2)	0.7587 (5)	0.0484 (9)
H3W	0.2066	0.9285	0.7362	0.073*
H4W	0.1188	0.9679	0.8342	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0192 (4)	0.0266 (4)	0.0139 (4)	−0.0005 (2)	0.0062 (3)	−0.0015 (2)
S1	0.0264 (5)	0.0180 (5)	0.0240 (5)	0.0012 (3)	0.0129 (4)	−0.0003 (3)
O1	0.0309 (15)	0.0283 (15)	0.0302 (15)	0.0046 (12)	0.0134 (12)	0.0053 (12)
O2	0.0311 (15)	0.0227 (15)	0.0398 (16)	−0.0025 (12)	0.0153 (13)	−0.0021 (12)
O3	0.0452 (18)	0.0300 (16)	0.0328 (15)	0.0003 (13)	0.0246 (14)	−0.0025 (12)
O4	0.0328 (16)	0.050 (2)	0.0276 (15)	0.0088 (14)	0.0110 (13)	−0.0041 (14)
N1	0.0320 (18)	0.0209 (17)	0.0281 (17)	−0.0011 (13)	0.0147 (15)	−0.0042 (13)
C1	0.0269 (19)	0.0205 (18)	0.0237 (18)	0.0017 (15)	0.0110 (15)	−0.0006 (14)
C2	0.036 (2)	0.021 (2)	0.042 (2)	−0.0019 (16)	0.023 (2)	−0.0006 (17)
C3	0.031 (2)	0.027 (2)	0.042 (2)	0.0011 (17)	0.0226 (19)	−0.0010 (17)
C4	0.028 (2)	0.0185 (18)	0.0210 (18)	0.0038 (14)	0.0081 (15)	0.0015 (14)
C5	0.031 (2)	0.025 (2)	0.032 (2)	−0.0039 (16)	0.0153 (17)	0.0010 (16)
C6	0.032 (2)	0.025 (2)	0.035 (2)	0.0006 (16)	0.0199 (18)	−0.0024 (16)
O5	0.0323 (17)	0.064 (2)	0.051 (2)	−0.0065 (16)	0.0208 (16)	−0.0216 (18)

Geometric parameters (Å, º) top

Mn1—O4	1.993 (3)	N1—H1A	0.9000
Mn1—O4ⁱ	1.993 (3)	N1—H1B	0.9000
Mn1—N1ⁱⁱ	2.058 (3)	C1—C2	1.383 (6)
Mn1—N1ⁱⁱⁱ	2.058 (3)	C1—C6	1.393 (6)
Mn1—O1ⁱ	2.425 (3)	C2—C3	1.385 (6)
Mn1—O1	2.425 (3)	C2—H2	0.9300
S1—O3	1.460 (3)	C3—C4	1.396 (6)
S1—O2	1.462 (3)	C3—H3	0.9300
S1—O1	1.467 (3)	C4—C5	1.390 (6)
S1—C1	1.780 (4)	C5—C6	1.387 (6)
O4—H1W	0.8200	C5—H5	0.9300
O4—H2W	0.8267	C6—H6	0.9300
N1—C4	1.453 (5)	O5—H3W	0.8197
N1—Mn1^iv	2.058 (3)	O5—H4W	0.8216

O4—Mn1—O4ⁱ	180	C4—N1—Mn1^iv	120.1 (2)
O4—Mn1—N1ⁱⁱ	92.95 (13)	C4—N1—H1A	107.3
O4ⁱ—Mn1—N1ⁱⁱ	87.05 (13)	Mn1^iv—N1—H1A	107.3
O4—Mn1—N1ⁱⁱⁱ	87.05 (13)	C4—N1—H1B	107.3
O4ⁱ—Mn1—N1ⁱⁱⁱ	92.95 (13)	Mn1^iv—N1—H1B	107.3
N1ⁱⁱ—Mn1—N1ⁱⁱⁱ	180	H1A—N1—H1B	106.9
O4—Mn1—O1ⁱ	84.94 (12)	C2—C1—C6	121.0 (4)
O4ⁱ—Mn1—O1ⁱ	95.06 (12)	C2—C1—S1	119.5 (3)
N1ⁱⁱ—Mn1—O1ⁱ	93.34 (11)	C6—C1—S1	119.5 (3)
N1ⁱⁱⁱ—Mn1—O1ⁱ	86.66 (11)	C1—C2—C3	119.8 (4)
O4—Mn1—O1	95.06 (12)	C1—C2—H2	120.1
O4ⁱ—Mn1—O1	84.94 (12)	C3—C2—H2	120.1
N1ⁱⁱ—Mn1—O1	86.66 (11)	C2—C3—C4	119.7 (4)
N1ⁱⁱⁱ—Mn1—O1	93.34 (11)	C2—C3—H3	120.1
O1ⁱ—Mn1—O1	180	C4—C3—H3	120.1
O3—S1—O2	113.12 (18)	C5—C4—C3	120.1 (4)
O3—S1—O1	111.46 (18)	C5—C4—N1	119.9 (4)
O2—S1—O1	111.50 (18)	C3—C4—N1	119.9 (4)
O3—S1—C1	106.85 (18)	C6—C5—C4	120.2 (4)
O2—S1—C1	106.57 (18)	C6—C5—H5	119.9
O1—S1—C1	106.90 (18)	C4—C5—H5	119.9
S1—O1—Mn1	129.61 (17)	C5—C6—C1	119.2 (4)
Mn1—O4—H1W	109.4	C5—C6—H6	120.4
Mn1—O4—H2W	132.0	C1—C6—H6	120.4
H1W—O4—H2W	111.8	H3W—O5—H4W	114.3

O3—S1—O1—Mn1	143.8 (2)	C6—C1—C2—C3	0.8 (6)
O2—S1—O1—Mn1	16.3 (3)	S1—C1—C2—C3	−176.6 (3)
C1—S1—O1—Mn1	−99.8 (2)	C1—C2—C3—C4	0.9 (6)
O4—Mn1—O1—S1	45.3 (2)	C2—C3—C4—C5	−2.4 (6)
O4ⁱ—Mn1—O1—S1	−134.7 (2)	C2—C3—C4—N1	176.5 (4)
N1ⁱⁱ—Mn1—O1—S1	−47.3 (2)	Mn1^iv—N1—C4—C5	−91.0 (4)
N1ⁱⁱⁱ—Mn1—O1—S1	132.7 (2)	Mn1^iv—N1—C4—C3	90.1 (4)
O3—S1—C1—C2	−141.2 (3)	C3—C4—C5—C6	2.1 (6)
O2—S1—C1—C2	−20.0 (4)	N1—C4—C5—C6	−176.8 (4)
O1—S1—C1—C2	99.4 (3)	C4—C5—C6—C1	−0.4 (6)
O3—S1—C1—C6	41.3 (4)	C2—C1—C6—C5	−1.1 (6)
O2—S1—C1—C6	162.5 (3)	S1—C1—C6—C5	176.4 (3)
O1—S1—C1—C6	−78.2 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^iv	0.90	2.46	2.980 (4)	117
O5—H3W···O1	0.82	2.06	2.855 (5)	164
C2—H2···O2	0.93	2.54	2.920 (5)	105
N1—H1B···O2ⁱⁱⁱ	0.90	2.41	3.217 (4)	149
O4—H2W···O5^v	0.83	1.83	2.651 (5)	175
C2—H2···O5^v	0.93	2.53	3.431 (6)	164
O4—H1W···O3^vi	0.82	2.02	2.795 (4)	157
N1—H1A···O3^vii	0.90	2.24	3.070 (5)	153
C3—H3···O3^vii	0.93	2.55	3.300 (5)	138
O5—H4W···O2^viii	0.82	2.00	2.815 (5)	175

Symmetry codes: (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+3/2; (v) x+1, y, z; (vi) x, y, z−1; (vii) x+1/2, −y+3/2, z−1/2; (viii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Mn(C₆H₆NO₃S)₂(H₂O)₂]·2H₂O
M_r	471.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.4485 (8), 17.4102 (19), 7.6509 (9)
β (°)	116.688 (1)
V (Å³)	886.47 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.49 × 0.45 × 0.45

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.547, 0.625
No. of measured, independent and observed [I > 2σ(I)] reflections	6604, 1637, 1585
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.149, 1.11
No. of reflections	1637
No. of parameters	124
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −1.03

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—O4	1.993 (3)	Mn1—O1	2.425 (3)
Mn1—N1ⁱ	2.058 (3)

O4—Mn1—O4ⁱⁱ	180	O4—Mn1—O1	95.06 (12)
O4—Mn1—N1ⁱ	92.95 (13)	O4ⁱⁱ—Mn1—O1	84.94 (12)
O4—Mn1—N1ⁱⁱⁱ	87.05 (13)	N1ⁱ—Mn1—O1	86.66 (11)
N1ⁱ—Mn1—N1ⁱⁱⁱ	180	N1ⁱⁱⁱ—Mn1—O1	93.34 (11)
O4—Mn1—O1ⁱⁱ	84.94 (12)	O1ⁱⁱ—Mn1—O1	180

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^iv	0.90	2.46	2.980 (4)	116.9
O5—H3W···O1	0.82	2.06	2.855 (5)	164.2
C2—H2···O2	0.93	2.54	2.920 (5)	104.7
N1—H1B···O2ⁱⁱⁱ	0.90	2.41	3.217 (4)	149.2
O4—H2W···O5^v	0.83	1.83	2.651 (5)	175.4
C2—H2···O5^v	0.93	2.53	3.431 (6)	163.9
O4—H1W···O3^vi	0.82	2.02	2.795 (4)	156.9
N1—H1A···O3^vii	0.90	2.24	3.070 (5)	152.5
C3—H3···O3^vii	0.93	2.55	3.300 (5)	137.5
O5—H4W···O2^viii	0.82	2.00	2.815 (5)	174.7

Symmetry codes: (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+3/2; (v) x+1, y, z; (vi) x, y, z−1; (vii) x+1/2, −y+3/2, z−1/2; (viii) −x+1, −y+2, −z+2.

Acknowledgements

We thank the Natural Science Foundation of Henan Province and the Key Discipline Foundation of Zhoukou Normal University for financial support of this research.

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