Benzene-1,3-dicarb­oxy­lic acid–1,2-bis­(4-pyrid­yl)ethene (1/1)

Liu, D.; Li, N.-Y.

doi:10.1107/S1600536811043418

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3039

doi:10.1107/S1600536811043418

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Benzene-1,3-dicarboxylic acid–1,2-bis(4-pyridyl)ethene (1/1)

Dong Liu ^a ^* and Ni-Ya Li ^a

^aCollege of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, Anhui, People's Republic of China
^*Correspondence e-mail: dongliu@chnu.edu.cn

(Received 4 October 2011; accepted 19 October 2011; online 29 October 2011)

In the title compound, C₁₂H₁₀N₂·C₈H₆O₄, the asymmetric unit contains two halves of 1,2-bis(4-pyridyl)ethene (bpe) molecules and one benzene-1,3-dicarboxylic acid (1,3-H₂BDC) molecule. These bpe and 1,3-H₂BDC molecules are linked by classical O—H⋯N hydrogen bonds, forming an extended one-dimensional zigzag chain. Each chain is further linked with neighboring ones by π–π interactions between the pyridine and aromatic rings [centroid–centroid distances = 3.9306 (15) Å] and the pyridine rings of pairs of symmetry-related molecules [centroid–centroid distances = 3.5751 (15), 3.7350 (15) and 3.6882 (15) Å], with the formation of a three-dimensional supramolecular framework.

Related literature

For structures and properties of self-assembled supramolecular compounds, see: Lehn (1990 ). For hydrogen-bonding interactions and π–π interactions in supramolecular compounds, see: Biradha (2003 ); Shan & Jones (2003 ); Weyna et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₀N₂·C₈H₆O₄
M_r = 348.35
Triclinic, $[P \overline 1]$
a = 6.8331 (14) Å
b = 6.8804 (14) Å
c = 18.618 (4) Å
α = 99.47 (3)°
β = 93.87 (3)°
γ = 102.69 (3)°
V = 837.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.40 × 0.40 × 0.35 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.962, T_max = 0.967
8280 measured reflections
3054 independent reflections
2153 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.137
S = 1.06
3054 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.83	1.77	2.597 (2)	176
O3—H3⋯N2	0.83	1.79	2.618 (2)	176
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043418/rk2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043418/rk2306Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043418/rk2306Isup3.cml

checkCIF report

Comment top

In the past decades, the supramolecular synthesis of multicomponent organic materials has attracted considerable attention due to their functional properties (Lehn, 1990). The facile way of synthesizing these co-crystals is to employ the components containing complementary functional groups such as pyridine and carboxylic acid. Owing to the hydrogen-bonds and π–π stacking between these types of groups, several multicomponent cocrystals containing various network geometries were prepared using these two functional groups (Biradha, 2003; Shan & Jones, 2003; Weyna et al., 2009).

The hydrothermal reaction of 1,2-bis(4-pyridyl)ethene (bpe) with benzene-1,3-dicarboxylic acid (1,3-H₂BDC) resulted in the cocrystals of C₁₂H₁₀N₂.C₈H₆O₄, I. In I, the asymmetric unit is formed by two halves of bpe molecules and one 1,3-H₂BDC molecule (Fig. 1). These molecular units are linked by classical O–H···N hydrogen-bonds (O1–H1···N1ⁱⁱⁱ, O1···N1ⁱⁱⁱ = 2.597 (2)Å; O3–H3···N2, O3···N2 = 2.618 (2)Å) forming an extended one-dimensional zigzag chain (Table 1, Fig. 2). Furthermore, the adjacent one-dimensional chains are interconnected each other through π–π interactions between pairs of molecules [Cg1···Cg1^iv = 3.5751 (15)Å; Cg1···Cg3 = 3.9306 (15)Å; Cg2···Cg2^v = 3.7350 (15)Å; Cg2···Cg2^vi = 3.7350 (15)Å form a three-dimensional framework (Fig. 3). The Cg1, Cg2 and Cg3, are the centroids of the rings N1/C9-C13, N2/C15-C19 and C1-C6. Symmetry codes: (iii) -x+1, y, z; (iv) -x+1, -y+1, -z+2; (v) -x+1, -y+1, -z+1; (vi) -x+2, -y+1, -z+1 .

Related literature top

For structures and properties of self-assembled supermolecular compounds, see: Lehn (1990). For hydrogen-bonding interactions and π–π interactions in supermolecular compounds, see: Biradha (2003); Shan & Jones (2003); Weyna et al. (2009).

Experimental top

To a 10 mL Pyrex glass tube was loaded 1,2-bis(4-pyridyl)ethene (18 mg, 0.1 mmol), benzene-1,3-dicarboxylic acid (17 mg, 0.1 mmol) and 3 ml of H₂O. The tube was sealed and heated in an oven to 423 K for three days, and then cooled to ambient temperature at the rate of 5 K h^-1 to form yellow crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are presented at the 30% probability level. Symmetry codes: (i) -x+2, -y+2, -z+1; (ii): -x, -y+1, -z+2; (iii) x+1, y, z.
	Fig. 2. The one-dimensional zigzag chain linked by hydrogen-bonding interactions. The blue dashed lines represent the hydrogen-bonds.
	Fig. 3. The three-dimensional supramolecular framework linked by hydrogen-bonding interactions and π–π interactions. The blue and cyan dashed lines represent the hydrogen-bonds and π–π interactions, respectively.

Benzene-1,3-dicarboxylic acid111,2-bis(4-pyridyl)ethene (1/1) top

Crystal data top

C₁₂H₁₀N₂·C₈H₆O₄	Z = 2
M_r = 348.35	F(000) = 364
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8331 (14) Å	Cell parameters from 2779 reflections
b = 6.8804 (14) Å	θ = 3.1–25.4°
c = 18.618 (4) Å	µ = 0.10 mm⁻¹
α = 99.47 (3)°	T = 223 K
β = 93.87 (3)°	Block, yellow
γ = 102.69 (3)°	0.40 × 0.40 × 0.35 mm
V = 837.4 (3) Å³

Data collection top

Rigaku Mercury CCD diffractometer	3054 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.3°, θ_min = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −8→8
T_min = 0.962, T_max = 0.967	k = −7→8
8280 measured reflections	l = −22→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0616P)² + 0.1982P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3054 reflections	Δρ_max = 0.23 e Å⁻³
238 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (4)

Crystal data top

C₁₂H₁₀N₂·C₈H₆O₄	γ = 102.69 (3)°
M_r = 348.35	V = 837.4 (3) Å³
Triclinic, P1	Z = 2
a = 6.8331 (14) Å	Mo Kα radiation
b = 6.8804 (14) Å	µ = 0.10 mm⁻¹
c = 18.618 (4) Å	T = 223 K
α = 99.47 (3)°	0.40 × 0.40 × 0.35 mm
β = 93.87 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	3054 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2153 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.967	R_int = 0.037
8280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
3054 reflections	Δρ_min = −0.19 e Å⁻³
238 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	−0.1898 (3)	0.1743 (2)	0.81468 (9)	0.0437 (5)
H1	−0.2835	0.1999	0.8378	0.065*
O2	−0.2446 (3)	−0.0994 (3)	0.86694 (10)	0.0528 (5)
O3	0.5207 (2)	0.0878 (2)	0.62885 (9)	0.0417 (4)
H3	0.5796	0.1779	0.6079	0.063*
O4	0.4236 (3)	0.3460 (2)	0.69323 (9)	0.0495 (5)
N1	0.5203 (3)	0.2721 (3)	0.88516 (10)	0.0348 (5)
N2	0.6910 (3)	0.3812 (3)	0.56392 (10)	0.0353 (5)
C1	0.0121 (3)	−0.0583 (3)	0.78717 (11)	0.0306 (5)
C2	0.1342 (3)	0.0735 (3)	0.75112 (11)	0.0292 (5)
H2	0.1109	0.2030	0.7507	0.035*
C3	0.2909 (3)	0.0166 (3)	0.71557 (11)	0.0283 (5)
C4	0.3240 (3)	−0.1741 (3)	0.71652 (11)	0.0346 (5)
H4	0.4293	−0.2141	0.6925	0.041*
C5	0.2028 (4)	−0.3062 (3)	0.75262 (12)	0.0403 (6)
H5	0.2260	−0.4357	0.7530	0.048*
C6	0.0478 (4)	−0.2489 (3)	0.78806 (12)	0.0369 (6)
H6	−0.0337	−0.3389	0.8128	0.044*
C7	−0.1539 (3)	0.0031 (3)	0.82700 (12)	0.0347 (5)
C8	0.4193 (3)	0.1663 (3)	0.67866 (11)	0.0327 (5)
C9	0.4644 (3)	0.4451 (4)	0.88158 (12)	0.0380 (6)
H9	0.5339	0.5335	0.8533	0.046*
C10	0.3099 (3)	0.4988 (3)	0.91739 (12)	0.0372 (6)
H10	0.2752	0.6216	0.9132	0.045*
C11	0.2046 (3)	0.3725 (3)	0.95979 (11)	0.0334 (5)
C12	0.2643 (3)	0.1941 (4)	0.96377 (12)	0.0390 (6)
H12	0.1989	0.1041	0.9923	0.047*
C13	0.4199 (3)	0.1495 (4)	0.92569 (12)	0.0379 (6)
H13	0.4568	0.0270	0.9284	0.046*
C14	0.0399 (3)	0.4214 (4)	1.00081 (13)	0.0391 (6)
H14	−0.0139	0.3314	1.0313	0.047*
C15	0.7001 (3)	0.3777 (3)	0.49225 (12)	0.0342 (5)
H15	0.6506	0.2538	0.4597	0.041*
C16	0.7789 (3)	0.5474 (3)	0.46388 (12)	0.0332 (5)
H16	0.7805	0.5380	0.4130	0.040*
C17	0.8558 (3)	0.7326 (3)	0.51039 (12)	0.0324 (5)
C18	0.8411 (3)	0.7367 (4)	0.58473 (12)	0.0383 (6)
H18	0.8865	0.8590	0.6184	0.046*
C19	0.7600 (3)	0.5615 (4)	0.60859 (12)	0.0404 (6)
H19	0.7522	0.5677	0.6591	0.049*
C20	0.9500 (3)	0.9104 (3)	0.48071 (12)	0.0353 (5)
H20	0.9390	0.8969	0.4294	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0436 (11)	0.0443 (10)	0.0532 (10)	0.0215 (8)	0.0243 (8)	0.0151 (8)
O2	0.0570 (12)	0.0512 (11)	0.0617 (11)	0.0181 (9)	0.0331 (9)	0.0247 (9)
O3	0.0466 (11)	0.0339 (9)	0.0481 (10)	0.0108 (8)	0.0249 (8)	0.0073 (8)
O4	0.0646 (12)	0.0296 (10)	0.0625 (11)	0.0167 (8)	0.0341 (9)	0.0129 (8)
N1	0.0284 (11)	0.0395 (11)	0.0360 (10)	0.0086 (9)	0.0060 (8)	0.0037 (9)
N2	0.0294 (11)	0.0360 (11)	0.0406 (11)	0.0080 (8)	0.0077 (8)	0.0058 (9)
C1	0.0326 (12)	0.0319 (12)	0.0271 (11)	0.0088 (10)	0.0034 (9)	0.0033 (9)
C2	0.0339 (13)	0.0262 (11)	0.0285 (11)	0.0099 (10)	0.0037 (9)	0.0038 (9)
C3	0.0305 (12)	0.0267 (11)	0.0278 (11)	0.0087 (9)	0.0033 (9)	0.0024 (9)
C4	0.0389 (14)	0.0348 (13)	0.0330 (12)	0.0150 (11)	0.0077 (10)	0.0049 (10)
C5	0.0506 (16)	0.0309 (13)	0.0443 (14)	0.0174 (12)	0.0113 (11)	0.0074 (11)
C6	0.0436 (15)	0.0317 (12)	0.0378 (13)	0.0094 (11)	0.0097 (10)	0.0103 (10)
C7	0.0343 (13)	0.0349 (13)	0.0348 (12)	0.0085 (11)	0.0055 (10)	0.0049 (10)
C8	0.0341 (13)	0.0335 (13)	0.0324 (12)	0.0127 (10)	0.0082 (9)	0.0035 (10)
C9	0.0341 (13)	0.0397 (14)	0.0416 (13)	0.0083 (11)	0.0118 (10)	0.0091 (11)
C10	0.0361 (14)	0.0354 (13)	0.0423 (13)	0.0121 (11)	0.0096 (10)	0.0060 (11)
C11	0.0289 (12)	0.0397 (13)	0.0293 (11)	0.0080 (10)	0.0022 (9)	0.0003 (10)
C12	0.0383 (14)	0.0419 (14)	0.0396 (13)	0.0112 (11)	0.0115 (10)	0.0103 (11)
C13	0.0353 (14)	0.0399 (13)	0.0413 (13)	0.0149 (11)	0.0059 (10)	0.0063 (11)
C14	0.0341 (13)	0.0451 (14)	0.0398 (12)	0.0111 (11)	0.0133 (10)	0.0067 (11)
C15	0.0281 (12)	0.0332 (13)	0.0408 (13)	0.0094 (10)	0.0055 (9)	0.0018 (10)
C16	0.0299 (12)	0.0346 (13)	0.0356 (12)	0.0105 (10)	0.0035 (9)	0.0037 (10)
C17	0.0246 (12)	0.0319 (12)	0.0394 (12)	0.0067 (10)	0.0016 (9)	0.0037 (10)
C18	0.0349 (13)	0.0347 (13)	0.0385 (13)	0.0006 (11)	0.0038 (10)	−0.0021 (11)
C19	0.0360 (14)	0.0473 (15)	0.0344 (12)	0.0041 (11)	0.0074 (10)	0.0036 (11)
C20	0.0332 (13)	0.0345 (12)	0.0387 (13)	0.0082 (10)	0.0028 (10)	0.0083 (10)

Geometric parameters (Å, º) top

O1—C7	1.307 (3)	C9—C10	1.371 (3)
O1—H1	0.8300	C9—H9	0.9400
O2—C7	1.215 (3)	C10—C11	1.387 (3)
O3—C8	1.310 (2)	C10—H10	0.9400
O3—H3	0.8300	C11—C12	1.387 (3)
O4—C8	1.215 (3)	C11—C14	1.470 (3)
N1—C13	1.333 (3)	C12—C13	1.378 (3)
N1—C9	1.338 (3)	C12—H12	0.9400
N2—C15	1.336 (3)	C13—H13	0.9400
N2—C19	1.343 (3)	C14—C14ⁱ	1.318 (5)
C1—C2	1.383 (3)	C14—H14	0.9400
C1—C6	1.387 (3)	C15—C16	1.378 (3)
C1—C7	1.495 (3)	C15—H15	0.9400
C2—C3	1.390 (3)	C16—C17	1.390 (3)
C2—H2	0.9400	C16—H16	0.9400
C3—C4	1.383 (3)	C17—C18	1.390 (3)
C3—C8	1.490 (3)	C17—C20	1.463 (3)
C4—C5	1.382 (3)	C18—C19	1.369 (3)
C4—H4	0.9400	C18—H18	0.9400
C5—C6	1.381 (3)	C19—H19	0.9400
C5—H5	0.9400	C20—C20ⁱⁱ	1.333 (4)
C6—H6	0.9400	C20—H20	0.9400

C7—O1—H1	109.5	C9—C10—H10	119.9
C8—O3—H3	109.5	C11—C10—H10	119.9
C13—N1—C9	117.51 (19)	C10—C11—C12	116.8 (2)
C15—N2—C19	116.9 (2)	C10—C11—C14	123.4 (2)
C2—C1—C6	119.4 (2)	C12—C11—C14	119.8 (2)
C2—C1—C7	121.13 (19)	C13—C12—C11	119.7 (2)
C6—C1—C7	119.4 (2)	C13—C12—H12	120.2
C1—C2—C3	120.74 (19)	C11—C12—H12	120.2
C1—C2—H2	119.6	N1—C13—C12	123.1 (2)
C3—C2—H2	119.6	N1—C13—H13	118.5
C4—C3—C2	119.2 (2)	C12—C13—H13	118.5
C4—C3—C8	122.45 (19)	C14ⁱ—C14—C11	126.6 (3)
C2—C3—C8	118.30 (18)	C14ⁱ—C14—H14	116.7
C5—C4—C3	120.3 (2)	C11—C14—H14	116.7
C5—C4—H4	119.9	N2—C15—C16	123.0 (2)
C3—C4—H4	119.9	N2—C15—H15	118.5
C6—C5—C4	120.3 (2)	C16—C15—H15	118.5
C6—C5—H5	119.9	C15—C16—C17	120.1 (2)
C4—C5—H5	119.9	C15—C16—H16	120.0
C5—C6—C1	120.1 (2)	C17—C16—H16	120.0
C5—C6—H6	120.0	C16—C17—C18	116.7 (2)
C1—C6—H6	120.0	C16—C17—C20	120.1 (2)
O2—C7—O1	124.3 (2)	C18—C17—C20	123.1 (2)
O2—C7—C1	121.9 (2)	C19—C18—C17	119.6 (2)
O1—C7—C1	113.81 (19)	C19—C18—H18	120.2
O4—C8—O3	123.6 (2)	C17—C18—H18	120.2
O4—C8—C3	121.53 (19)	N2—C19—C18	123.7 (2)
O3—C8—C3	114.84 (18)	N2—C19—H19	118.2
N1—C9—C10	122.7 (2)	C18—C19—H19	118.2
N1—C9—H9	118.6	C20ⁱⁱ—C20—C17	126.3 (3)
C10—C9—H9	118.6	C20ⁱⁱ—C20—H20	116.8
C9—C10—C11	120.2 (2)	C17—C20—H20	116.8

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱⁱⁱ	0.83	1.77	2.597 (2)	176
O3—H3···N2	0.83	1.79	2.618 (2)	176

Symmetry code: (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂·C₈H₆O₄
M_r	348.35
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	6.8331 (14), 6.8804 (14), 18.618 (4)
α, β, γ (°)	99.47 (3), 93.87 (3), 102.69 (3)
V (Å³)	837.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.40 × 0.35

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.962, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	8280, 3054, 2153
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.137, 1.06
No. of reflections	3054
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.83	1.77	2.597 (2)	175.8
O3—H3···N2	0.83	1.79	2.618 (2)	175.6

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the Research Start-Up Fund for New Staff of Huaibei Normal University (grant No. 600581).

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