N′-[(E)-2-Hy­droxy-5-iodo­benzyl­idene]-4-methyl­benzene­sulfono­hydrazide

Ghorbanloo, M.; Notash, B.

doi:10.1107/S1600536812035738

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2760

doi:10.1107/S1600536812035738

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N′-[(E)-2-Hydroxy-5-iodobenzylidene]-4-methylbenzenesulfonohydrazide

Massomeh Ghorbanloo ^a ^* and Behrouz Notash ^b

^aDepartment of Chemistry, Faculty of Science, University of Zanjan, 45371-38791 Zanjan, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: m_ghorbanloo@yahoo.com

(Received 1 August 2012; accepted 14 August 2012; online 23 August 2012)

In the title molecule, C₁₄H₁₃IN₂O₃S, the dihedral angle between the planes of the benzene and toluene rings is 84.3 (3)°. The molecule displays a trans conformation with respect to the C=N bond. There is an intramolecular O—H⋯N hydrogen bond with the azomethine N atom as acceptor. In the crystal, N—H⋯O hydrogen bonds connect the molecules into chains running along the b axis.

Related literature

For background to sulfonamides, see: Kayser et al. (2004 ). For related structures and their applications, see: Shahverdizadeh et al. (2011 ); Ali et al. (2007 ); Tierney et al. (2006 ); Silva et al. (2006 ). For polymorphism in sulfonohydrazides, see: Kia et al. (2008 ); Tai et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₃IN₂O₃S
M_r = 416.23
Monoclinic, P 2₁
a = 6.2467 (12) Å
b = 10.394 (2) Å
c = 11.971 (2) Å
β = 92.42 (3)°
V = 776.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.21 mm⁻¹
T = 298 K
0.50 × 0.40 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.405, T_max = 0.667
6035 measured reflections
3841 independent reflections
2791 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.114
S = 0.92
3841 reflections
197 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.99 e Å⁻³
Absolute structure: Flack (1983 ), 1641 Friedel pairs
Flack parameter: −0.06 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A⋯O1ⁱ	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812035738/bt5993sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035738/bt5993Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035738/bt5993Isup3.cml

checkCIF report

Comment top

Sulfonyl hydrazones are found to exhibit large medicinal applications. Similar to sulfonamides, sulfonyl hydrazones also have various biological activities (Kayser et al., 2004). For example, imidosulfonylhydrazones have antibacterial and antineociceptive properties (Silva et al., 2006). Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory activities. On the other hand, polymorphism is a phenomenon wherein the same substances exhibits different crystal packing arrangements and is of practical importance e.g., pharmaceutical processes where different physical properties of polymorphic forms can substantially alter the viability and quality of product. Plymorphism is another interesting subject in sulfonyl hydrazones. sulfonyl hydrazones derived from the condensation of O-hydroxy aldehydes and sulfonyl acid hydrazides can form different polymorphs. Kia et al. (2008) and Tai et al. (2009) have reported two polymorph of these type of compounds.

We report here the crystal structure of (E)-N'-(2-hydroxy-5-iodobenzylidene)-4-methylbenzenesulfonohydrazide. The asymmetric unit of the title compound contains one molecule, which is shown in Fig. 1. Bond distances and bond angles are in the normal range of similar compounds (Shahverdizadeh et al., 2011; Ali et al., 2007; Tierney et al., 2006). The molecule displays trans configuration with respect to the C=N bond. The packing diagram of the title compound is shown in Fig. 2. In the title compound, the dihedral angle between the planes of benzene and toluene rings is 84.3 (3)°. There is an intramolecular O—H···N hydrogen bond in which the nitrogen of the azomethine group (–C=N–) acting as hydrogen bond acceptor. Intermolecular N—H···O hydrogen bond stabilize the crystal structure (Fig. 2 & Table 1).

Related literature top

For background to sulfonamides, see: Kayser et al. (2004). For related structures and their applications, see: Shahverdizadeh et al. (2011); Ali et al. (2007); Tierney et al. (2006); Silva et al. (2006). For polymorphism in sulfonohydrazides, see: Kia et al. (2008); Tai et al. (2009).

Experimental top

For preparing the title compound, a methanol (10 ml) solution of 2-hydroxy-5-iodobenzaldehyde (2 mmol) was dropwise added to a methanol solution (10 ml) of 4-methyl-benzenesulfonic acid hydrazide (2 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature. A white precipitate of the title compound was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 90%. Selected IR (cm^-1): 3464 (w, broad), 3140 (m), 1619 (s), 1481 (vs), 1359 (s), 1329 (vs), 1264 (vs), 1177 (s), 1087 (s), 956 (vs), 869 (vs) 772 (s), 666 (s), 545 (s), 458 (m).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

The molecular structure of the title compound with atom labels. Anisotropic displacement ellipsoids drawn at 30% probability level for non-H atoms.

The packing diagram of the title compound. Hydrogen bonds are shown as blue dashed line.

N'-[(E)-2-Hydroxy-5-iodobenzylidene]-4- methylbenzenesulfonohydrazide top

Crystal data top

C₁₄H₁₃IN₂O₃S	F(000) = 408
M_r = 416.23	D_x = 1.780 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3841 reflections
a = 6.2467 (12) Å	θ = 1.7–29.2°
b = 10.394 (2) Å	µ = 2.21 mm⁻¹
c = 11.971 (2) Å	T = 298 K
β = 92.42 (3)°	Plate, colorless
V = 776.6 (3) Å³	0.50 × 0.40 × 0.20 mm
Z = 2

Data collection top

Stoe IPDS 2 diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	2791 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 1.7°
rotation method scans	h = −7→8
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −14→13
T_min = 0.405, T_max = 0.667	l = −16→16
6035 measured reflections

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.071P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
3841 reflections	Δρ_max = 0.88 e Å⁻³
197 parameters	Δρ_min = −0.99 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1641 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Crystal data top

C₁₄H₁₃IN₂O₃S	V = 776.6 (3) Å³
M_r = 416.23	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.2467 (12) Å	µ = 2.21 mm⁻¹
b = 10.394 (2) Å	T = 298 K
c = 11.971 (2) Å	0.50 × 0.40 × 0.20 mm
β = 92.42 (3)°

Data collection top

Stoe IPDS 2 diffractometer	3841 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	2791 reflections with I > 2σ(I)
T_min = 0.405, T_max = 0.667	R_int = 0.059
6035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	Δρ_max = 0.88 e Å⁻³
S = 0.92	Δρ_min = −0.99 e Å⁻³
3841 reflections	Absolute structure: Flack (1983), 1641 Friedel pairs
197 parameters	Absolute structure parameter: −0.06 (3)
3 restraints

Special details top

Experimental. shape of crystal determined optically

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
I1	0.80088 (6)	0.64270 (4)	−0.32973 (4)	0.07048 (17)
S1	−0.2369 (2)	0.51804 (13)	0.17826 (10)	0.0423 (3)
O1	0.2908 (7)	0.3287 (4)	0.0117 (4)	0.0493 (9)
O2	−0.1752 (7)	0.3869 (4)	0.1850 (4)	0.0584 (11)
O3	−0.4564 (6)	0.5561 (4)	0.1806 (4)	0.0566 (10)
N1	0.0354 (7)	0.5237 (4)	0.0251 (3)	0.0387 (9)
N2	−0.1570 (7)	0.5714 (4)	0.0580 (4)	0.0427 (10)
C1	0.6247 (8)	0.5391 (5)	−0.2153 (4)	0.0437 (12)
C2	0.6906 (8)	0.4168 (6)	−0.1848 (4)	0.0452 (12)
H2	0.8103	0.3806	−0.2161	0.054*
C3	0.5781 (9)	0.3485 (5)	−0.1074 (5)	0.0455 (12)
H3	0.6245	0.2672	−0.0849	0.055*
C4	0.3963 (8)	0.4012 (5)	−0.0633 (4)	0.0377 (10)
C5	0.3257 (8)	0.5256 (5)	−0.0950 (4)	0.0369 (10)
C6	0.4431 (8)	0.5934 (5)	−0.1716 (4)	0.0406 (11)
H6	0.3999	0.6755	−0.1937	0.049*
C7	0.1345 (8)	0.5822 (5)	−0.0518 (4)	0.0374 (10)
H7	0.0837	0.6605	−0.0795	0.045*
C8	−0.0891 (8)	0.6054 (5)	0.2828 (4)	0.0420 (12)
C9	−0.1739 (10)	0.7173 (5)	0.3242 (5)	0.0456 (12)
H9	−0.3088	0.7457	0.2992	0.055*
C10	−0.0552 (11)	0.7865 (6)	0.4035 (5)	0.0543 (15)
H10	−0.1116	0.8620	0.4317	0.065*
C11	0.1458 (11)	0.7461 (6)	0.4418 (5)	0.0543 (14)
C12	0.2764 (15)	0.8255 (10)	0.5268 (7)	0.082 (2)
H12A	0.2910	0.7791	0.5960	0.123*
H12B	0.2049	0.9058	0.5390	0.123*
H12C	0.4158	0.8419	0.4991	0.123*
C13	0.2264 (9)	0.6346 (9)	0.3970 (5)	0.0598 (14)
H13	0.3618	0.6065	0.4214	0.072*
C14	0.1134 (10)	0.5641 (6)	0.3177 (5)	0.0532 (14)
H14	0.1717	0.4899	0.2880	0.064*
H1	0.173 (6)	0.359 (7)	0.024 (6)	0.064*
H2A	−0.186 (11)	0.649 (3)	0.037 (6)	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0614 (2)	0.0783 (3)	0.0737 (3)	−0.0046 (3)	0.02653 (18)	0.0203 (3)
S1	0.0421 (7)	0.0388 (6)	0.0469 (6)	−0.0040 (5)	0.0134 (5)	−0.0008 (5)
O1	0.057 (2)	0.0328 (19)	0.060 (2)	0.0003 (17)	0.019 (2)	0.0067 (16)
O2	0.070 (3)	0.042 (2)	0.064 (3)	−0.007 (2)	0.012 (2)	0.0030 (18)
O3	0.040 (2)	0.063 (2)	0.068 (2)	−0.0066 (18)	0.0153 (18)	−0.008 (2)
N1	0.041 (2)	0.036 (2)	0.040 (2)	0.0023 (18)	0.0073 (17)	−0.0028 (17)
N2	0.044 (2)	0.041 (2)	0.044 (2)	0.002 (2)	0.0133 (19)	−0.0004 (19)
C1	0.042 (3)	0.050 (3)	0.039 (2)	−0.008 (2)	0.008 (2)	0.001 (2)
C2	0.038 (3)	0.047 (3)	0.050 (3)	0.002 (2)	0.007 (2)	−0.008 (2)
C3	0.044 (3)	0.037 (3)	0.056 (3)	0.004 (2)	0.007 (2)	−0.004 (2)
C4	0.042 (3)	0.030 (2)	0.041 (2)	−0.005 (2)	0.005 (2)	−0.0026 (19)
C5	0.038 (2)	0.037 (3)	0.035 (2)	−0.006 (2)	0.0018 (19)	−0.002 (2)
C6	0.045 (3)	0.035 (2)	0.042 (2)	0.002 (2)	0.005 (2)	0.0055 (19)
C7	0.043 (3)	0.029 (2)	0.041 (2)	0.001 (2)	0.004 (2)	−0.0008 (18)
C8	0.039 (3)	0.044 (3)	0.044 (2)	−0.004 (2)	0.015 (2)	0.0020 (19)
C9	0.046 (3)	0.043 (3)	0.048 (3)	0.004 (2)	0.005 (2)	0.004 (2)
C10	0.067 (4)	0.047 (3)	0.051 (3)	0.002 (3)	0.018 (3)	−0.007 (2)
C11	0.060 (4)	0.064 (4)	0.040 (3)	−0.014 (3)	0.011 (2)	0.001 (3)
C12	0.086 (6)	0.099 (6)	0.059 (4)	0.000 (5)	−0.008 (4)	−0.013 (4)
C13	0.047 (3)	0.077 (4)	0.055 (3)	0.011 (4)	0.005 (2)	0.011 (4)
C14	0.050 (3)	0.052 (3)	0.059 (3)	0.007 (3)	0.013 (3)	−0.003 (3)

Geometric parameters (Å, º) top

I1—C1	2.092 (5)	C5—C7	1.447 (7)
S1—O2	1.418 (5)	C6—H6	0.9300
S1—O3	1.429 (4)	C7—H7	0.9300
S1—N2	1.640 (4)	C8—C9	1.379 (7)
S1—C8	1.774 (5)	C8—C14	1.384 (8)
O1—C4	1.364 (6)	C9—C10	1.381 (9)
O1—H1	0.82 (2)	C9—H9	0.9300
N1—C7	1.283 (6)	C10—C11	1.384 (9)
N1—N2	1.373 (6)	C10—H10	0.9300
N2—H2A	0.86 (2)	C11—C13	1.380 (11)
C1—C2	1.380 (8)	C11—C12	1.521 (11)
C1—C6	1.389 (7)	C12—H12A	0.9600
C2—C3	1.382 (8)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.385 (7)	C13—C14	1.371 (10)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.413 (7)	C14—H14	0.9300
C5—C6	1.390 (6)

O2—S1—O3	121.6 (3)	C5—C6—H6	119.9
O2—S1—N2	106.4 (2)	N1—C7—C5	119.6 (4)
O3—S1—N2	104.6 (3)	N1—C7—H7	120.2
O2—S1—C8	108.7 (3)	C5—C7—H7	120.2
O3—S1—C8	108.4 (2)	C9—C8—C14	120.9 (5)
N2—S1—C8	106.1 (2)	C9—C8—S1	119.3 (4)
C4—O1—H1	111 (5)	C14—C8—S1	119.7 (4)
C7—N1—N2	119.3 (4)	C8—C9—C10	118.9 (6)
N1—N2—S1	115.6 (3)	C8—C9—H9	120.6
N1—N2—H2A	115 (5)	C10—C9—H9	120.6
S1—N2—H2A	120 (5)	C9—C10—C11	121.5 (6)
C2—C1—C6	120.9 (5)	C9—C10—H10	119.2
C2—C1—I1	119.2 (4)	C11—C10—H10	119.2
C6—C1—I1	119.8 (4)	C13—C11—C10	117.8 (6)
C1—C2—C3	119.7 (5)	C13—C11—C12	121.4 (7)
C1—C2—H2	120.1	C10—C11—C12	120.7 (7)
C3—C2—H2	120.1	C11—C12—H12A	109.5
C2—C3—C4	120.0 (5)	C11—C12—H12B	109.5
C2—C3—H3	120.0	H12A—C12—H12B	109.5
C4—C3—H3	120.0	C11—C12—H12C	109.5
O1—C4—C3	117.3 (5)	H12A—C12—H12C	109.5
O1—C4—C5	121.9 (4)	H12B—C12—H12C	109.5
C3—C4—C5	120.8 (5)	C14—C13—C11	122.1 (6)
C6—C5—C4	118.3 (4)	C14—C13—H13	118.9
C6—C5—C7	119.8 (5)	C11—C13—H13	118.9
C4—C5—C7	122.0 (4)	C13—C14—C8	118.7 (6)
C1—C6—C5	120.3 (5)	C13—C14—H14	120.6
C1—C6—H6	119.9	C8—C14—H14	120.6

C7—N1—N2—S1	−162.9 (4)	C6—C5—C7—N1	−174.8 (5)
O2—S1—N2—N1	−36.8 (5)	C4—C5—C7—N1	6.4 (7)
O3—S1—N2—N1	−166.7 (4)	O2—S1—C8—C9	−153.8 (4)
C8—S1—N2—N1	78.8 (4)	O3—S1—C8—C9	−19.8 (5)
C6—C1—C2—C3	−1.7 (8)	N2—S1—C8—C9	92.0 (4)
I1—C1—C2—C3	178.6 (4)	O2—S1—C8—C14	29.4 (5)
C1—C2—C3—C4	1.9 (8)	O3—S1—C8—C14	163.4 (4)
C2—C3—C4—O1	179.3 (5)	N2—S1—C8—C14	−84.8 (5)
C2—C3—C4—C5	−1.1 (8)	C14—C8—C9—C10	−1.5 (8)
O1—C4—C5—C6	179.7 (5)	S1—C8—C9—C10	−178.3 (4)
C3—C4—C5—C6	0.1 (7)	C8—C9—C10—C11	0.1 (8)
O1—C4—C5—C7	−1.5 (7)	C9—C10—C11—C13	0.9 (9)
C3—C4—C5—C7	179.0 (5)	C9—C10—C11—C12	178.4 (6)
C2—C1—C6—C5	0.7 (8)	C10—C11—C13—C14	−0.5 (9)
I1—C1—C6—C5	−179.6 (4)	C12—C11—C13—C14	−177.9 (7)
C4—C5—C6—C1	0.1 (7)	C11—C13—C14—C8	−0.9 (10)
C7—C5—C6—C1	−178.8 (5)	C9—C8—C14—C13	1.9 (8)
N2—N1—C7—C5	−173.7 (4)	S1—C8—C14—C13	178.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A···O1ⁱ	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)

Symmetry code: (i) −x, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃IN₂O₃S
M_r	416.23
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.2467 (12), 10.394 (2), 11.971 (2)
β (°)	92.42 (3)
V (Å³)	776.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.21
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.405, 0.667
No. of measured, independent and observed [I > 2σ(I)] reflections	6035, 3841, 2791
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.114, 0.92
No. of reflections	3841
No. of parameters	197
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.99
Absolute structure	Flack (1983), 1641 Friedel pairs
Absolute structure parameter	−0.06 (3)

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A···O1ⁱ	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)

Symmetry code: (i) −x, y+1/2, −z.

Acknowledgements

The authors are grateful to the University of Zanjan for financial support.

References

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