4-(3,4-Diacetyl-5-methyl-1H-pyrazol-1-yl)benzene­sulfonamide

Abdel-Aziz, H.A.; Bari, A.; Ng, S.W.

doi:10.1107/S1600536811005733

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o693

doi:10.1107/S1600536811005733

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4-(3,4-Diacetyl-5-methyl-1H-pyrazol-1-yl)benzenesulfonamide

Hatem A. Abdel-Aziz,^a Ahmed Bari ^a and Seik Weng Ng ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 February 2011; accepted 16 February 2011; online 23 February 2011)

In the title molecule, C₁₄H₁₅N₃O₄S, the pyrazole ring is aligned at a dihedral angle of 55.5 (1)° with respect to the benzene ring; the mean planes of the acetyl substituents are twisted by 13.4 (3) and 30.1 (3)° with respect to the pyrazole ring. Intermolecular classical N—H⋯O and weak C—H⋯O hydrogen bonding links the molecules, forming a three-dimensional network architecture in the crystal structure.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₄S
M_r = 321.35
Orthorhombic, P n a 2₁
a = 8.3716 (3) Å
b = 21.7722 (8) Å
c = 7.8915 (3) Å
V = 1438.37 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.952, T_max = 0.988
10477 measured reflections
3087 independent reflections
2634 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.095
S = 1.05
3087 reflections
210 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1337 Friedel pairs
Flack parameter: 0.08 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯O2ⁱ	0.88 (1)	2.03 (1)	2.864 (3)	159 (3)
N3—H32⋯O4ⁱⁱ	0.88 (1)	2.06 (1)	2.933 (3)	170 (3)
C1—H1C⋯O3ⁱ	0.98	2.55	3.446 (3)	151
C10—H10⋯O1ⁱⁱⁱ	0.95	2.51	3.314 (3)	142
C14—H14⋯O1^iv	0.95	2.54	3.414 (3)	153
Symmetry codes: (i) $[-x+2, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) x-1, y, z; (iv) $[-x+3, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005733/xu5161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005733/xu5161Isup2.hkl

checkCIF report

Comment top

We have reported the antitumor activity of aryl-pyrazoles against CaCo-2 and HEP-2 cell lines (Abdel-Aziz et al., 2010). These compounds were synthesized by a cycloaddition under microwave conditions. The present study involves the synthesis of an aryl-pyrazole having a sulfonamide –SO₂NH₂ substituent (Scheme I) that is expected to improve aqueous solubility. The C₁₄H₁₅N₃O₄ molecule has two acetyl substitutents on the pyrazolyl ring along with a benzenesulfanomide group. The sulfonamido unit interacts with an adjacent acetyl and sulfonamido O-atoms to generate a three-dimensional network (Table 1).

Related literature top

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010).

Experimental top

1-Phenyl-2-(phenylsulfonyl)ethanone (0.26 g, 10 mmol) was dissolved in a sodium ethoxide solution (prepared by dissolving 0.23 g sodium metal in 50 ml absolute ethanol). To the solution was added (Z)-2-oxo-N'-(4-sulfamoylphenyl)propanehydrazonoyl chloride (0.28 g, 10 mmol). The mixture was stirred for 12 h. The mixuture was then poured into cold water; the solid product was collected and recrystallized from an ethanol-water (4:1) mixture.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₅N₃O₄S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(3,4-Diacetyl-5-methyl-1H-pyrazol-1-yl)benzenesulfonamide top

Crystal data top

C₁₄H₁₅N₃O₄S	F(000) = 672
M_r = 321.35	D_x = 1.484 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3291 reflections
a = 8.3716 (3) Å	θ = 2.4–29.2°
b = 21.7722 (8) Å	µ = 0.25 mm⁻¹
c = 7.8915 (3) Å	T = 100 K
V = 1438.37 (9) Å³	Prism, colorless
Z = 4	0.20 × 0.15 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3087 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2634 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.056
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −28→27
T_min = 0.952, T_max = 0.988	l = −10→9
10477 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0422P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3087 reflections	Δρ_max = 0.31 e Å⁻³
210 parameters	Δρ_min = −0.39 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1337 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (8)

Crystal data top

C₁₄H₁₅N₃O₄S	V = 1438.37 (9) Å³
M_r = 321.35	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.3716 (3) Å	µ = 0.25 mm⁻¹
b = 21.7722 (8) Å	T = 100 K
c = 7.8915 (3) Å	0.20 × 0.15 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3087 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2634 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.988	R_int = 0.056
10477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	Δρ_max = 0.31 e Å⁻³
S = 1.05	Δρ_min = −0.39 e Å⁻³
3087 reflections	Absolute structure: Flack (1983), 1337 Friedel pairs
210 parameters	Absolute structure parameter: 0.08 (8)
3 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.69022 (7)	0.29885 (3)	0.49994 (9)	0.01726 (16)
O1	1.5767 (2)	0.55022 (9)	0.1918 (3)	0.0278 (5)
O2	1.3205 (2)	0.68881 (8)	0.5594 (3)	0.0229 (5)
O3	0.7216 (2)	0.27511 (9)	0.6664 (3)	0.0234 (5)
O4	0.5323 (2)	0.31899 (7)	0.4576 (3)	0.0226 (5)
N1	1.0863 (2)	0.56565 (9)	0.4491 (3)	0.0164 (5)
N2	1.1261 (2)	0.50985 (9)	0.3847 (3)	0.0160 (5)
N3	0.7369 (3)	0.24582 (10)	0.3684 (3)	0.0182 (5)
H31	0.726 (3)	0.2569 (13)	0.2624 (17)	0.017 (8)*
H32	0.8310 (18)	0.2289 (11)	0.385 (4)	0.021 (8)*
C1	1.5821 (3)	0.64151 (12)	0.3508 (4)	0.0235 (7)
H1A	1.6916	0.6438	0.3072	0.035*
H1B	1.5845	0.6411	0.4750	0.035*
H1C	1.5215	0.6773	0.3115	0.035*
C2	1.5041 (3)	0.58395 (12)	0.2877 (4)	0.0196 (6)
C3	1.3404 (3)	0.56637 (11)	0.3441 (3)	0.0149 (6)
C4	1.2165 (3)	0.60007 (11)	0.4274 (3)	0.0157 (6)
C5	1.2032 (3)	0.66253 (11)	0.5028 (4)	0.0179 (5)
C6	1.0404 (3)	0.68993 (11)	0.5136 (5)	0.0252 (6)
H6A	1.0466	0.7299	0.5704	0.038*
H6B	0.9704	0.6625	0.5783	0.038*
H6C	0.9972	0.6954	0.3992	0.038*
C7	1.2751 (3)	0.50868 (12)	0.3166 (3)	0.0170 (6)
C8	1.3336 (3)	0.45309 (12)	0.2257 (4)	0.0236 (7)
H8A	1.2448	0.4339	0.1646	0.035*
H8B	1.3777	0.4238	0.3077	0.035*
H8C	1.4170	0.4650	0.1449	0.035*
C9	1.0197 (3)	0.45957 (11)	0.4118 (4)	0.0160 (6)
C10	0.8629 (3)	0.46375 (12)	0.3568 (3)	0.0176 (6)
H10	0.8261	0.4996	0.3002	0.021*
C11	0.7607 (3)	0.41477 (12)	0.3856 (4)	0.0196 (6)
H11	0.6525	0.4168	0.3498	0.024*
C12	0.8176 (3)	0.36269 (11)	0.4670 (3)	0.0172 (6)
C13	0.9744 (3)	0.35924 (11)	0.5236 (4)	0.0178 (6)
H13	1.0112	0.3236	0.5810	0.021*
C14	1.0763 (3)	0.40801 (11)	0.4958 (4)	0.0190 (6)
H14	1.1839	0.4063	0.5338	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0148 (3)	0.0163 (3)	0.0207 (4)	−0.0022 (2)	0.0012 (3)	0.0006 (3)
O1	0.0200 (10)	0.0241 (10)	0.0392 (13)	0.0012 (8)	0.0106 (10)	−0.0016 (10)
O2	0.0238 (11)	0.0223 (10)	0.0226 (12)	−0.0058 (8)	0.0029 (8)	−0.0047 (9)
O3	0.0263 (10)	0.0229 (10)	0.0211 (12)	−0.0025 (9)	0.0023 (9)	0.0001 (9)
O4	0.0157 (9)	0.0188 (9)	0.0334 (14)	−0.0020 (7)	0.0016 (8)	0.0017 (9)
N1	0.0164 (11)	0.0135 (10)	0.0192 (13)	0.0009 (8)	0.0006 (9)	−0.0009 (9)
N2	0.0147 (11)	0.0159 (10)	0.0175 (12)	0.0008 (9)	−0.0015 (9)	−0.0025 (10)
N3	0.0192 (12)	0.0160 (11)	0.0192 (14)	−0.0004 (9)	−0.0017 (10)	0.0022 (11)
C1	0.0171 (13)	0.0244 (14)	0.0289 (18)	−0.0047 (11)	0.0023 (12)	−0.0023 (14)
C2	0.0170 (13)	0.0203 (14)	0.0215 (16)	0.0011 (11)	−0.0017 (12)	0.0043 (14)
C3	0.0143 (12)	0.0174 (13)	0.0132 (15)	−0.0004 (10)	−0.0010 (10)	0.0031 (11)
C4	0.0165 (12)	0.0173 (12)	0.0134 (14)	−0.0015 (10)	−0.0011 (11)	0.0011 (12)
C5	0.0242 (13)	0.0162 (12)	0.0134 (13)	−0.0016 (10)	0.0032 (13)	0.0016 (14)
C6	0.0255 (14)	0.0191 (13)	0.0312 (18)	0.0020 (11)	0.0024 (15)	−0.0052 (14)
C7	0.0155 (13)	0.0180 (13)	0.0176 (15)	−0.0002 (10)	−0.0017 (11)	0.0026 (12)
C8	0.0190 (13)	0.0197 (14)	0.0321 (19)	−0.0007 (11)	0.0051 (12)	−0.0050 (13)
C9	0.0163 (12)	0.0147 (12)	0.0170 (15)	−0.0027 (10)	0.0032 (11)	−0.0048 (11)
C10	0.0173 (13)	0.0151 (12)	0.0204 (16)	0.0021 (10)	0.0002 (11)	−0.0003 (12)
C11	0.0118 (12)	0.0241 (13)	0.0229 (16)	0.0013 (11)	−0.0031 (11)	−0.0012 (14)
C12	0.0165 (12)	0.0158 (12)	0.0193 (17)	0.0001 (10)	0.0031 (11)	−0.0017 (12)
C13	0.0179 (12)	0.0150 (12)	0.0207 (16)	0.0032 (10)	−0.0021 (11)	0.0007 (12)
C14	0.0157 (12)	0.0189 (12)	0.0224 (15)	0.0016 (10)	−0.0001 (13)	−0.0040 (13)

Geometric parameters (Å, º) top

S1—O4	1.4325 (18)	C4—C5	1.489 (3)
S1—O3	1.436 (2)	C5—C6	1.490 (3)
S1—N3	1.601 (3)	C6—H6A	0.9800
S1—C12	1.771 (2)	C6—H6B	0.9800
O1—C2	1.218 (3)	C6—H6C	0.9800
O2—C5	1.221 (3)	C7—C8	1.490 (4)
N1—C4	1.334 (3)	C8—H8A	0.9800
N1—N2	1.358 (3)	C8—H8B	0.9800
N2—C7	1.358 (3)	C8—H8C	0.9800
N2—C9	1.427 (3)	C9—C10	1.385 (3)
N3—H31	0.875 (10)	C9—C14	1.387 (4)
N3—H32	0.879 (10)	C10—C11	1.386 (4)
C1—C2	1.498 (4)	C10—H10	0.9500
C1—H1A	0.9800	C11—C12	1.388 (4)
C1—H1B	0.9800	C11—H11	0.9500
C1—H1C	0.9800	C12—C13	1.388 (3)
C2—C3	1.491 (4)	C13—C14	1.380 (3)
C3—C7	1.387 (3)	C13—H13	0.9500
C3—C4	1.430 (4)	C14—H14	0.9500

O4—S1—O3	119.48 (11)	C5—C6—H6B	109.5
O4—S1—N3	107.16 (12)	H6A—C6—H6B	109.5
O3—S1—N3	106.79 (13)	C5—C6—H6C	109.5
O4—S1—C12	106.35 (11)	H6A—C6—H6C	109.5
O3—S1—C12	107.84 (12)	H6B—C6—H6C	109.5
N3—S1—C12	108.90 (12)	N2—C7—C3	106.5 (2)
C4—N1—N2	104.7 (2)	N2—C7—C8	120.5 (2)
N1—N2—C7	112.94 (19)	C3—C7—C8	132.9 (2)
N1—N2—C9	118.5 (2)	C7—C8—H8A	109.5
C7—N2—C9	128.2 (2)	C7—C8—H8B	109.5
S1—N3—H31	113 (2)	H8A—C8—H8B	109.5
S1—N3—H32	115.2 (19)	C7—C8—H8C	109.5
H31—N3—H32	110 (3)	H8A—C8—H8C	109.5
C2—C1—H1A	109.5	H8B—C8—H8C	109.5
C2—C1—H1B	109.5	C10—C9—C14	121.8 (2)
H1A—C1—H1B	109.5	C10—C9—N2	119.6 (2)
C2—C1—H1C	109.5	C14—C9—N2	118.6 (2)
H1A—C1—H1C	109.5	C9—C10—C11	118.9 (2)
H1B—C1—H1C	109.5	C9—C10—H10	120.6
O1—C2—C3	119.3 (2)	C11—C10—H10	120.6
O1—C2—C1	119.6 (2)	C10—C11—C12	119.5 (2)
C3—C2—C1	121.1 (2)	C10—C11—H11	120.2
C7—C3—C4	104.5 (2)	C12—C11—H11	120.2
C7—C3—C2	123.3 (2)	C11—C12—C13	121.2 (2)
C4—C3—C2	132.2 (2)	C11—C12—S1	120.17 (19)
N1—C4—C3	111.3 (2)	C13—C12—S1	118.66 (19)
N1—C4—C5	113.6 (2)	C14—C13—C12	119.5 (2)
C3—C4—C5	135.0 (2)	C14—C13—H13	120.3
O2—C5—C4	120.9 (2)	C12—C13—H13	120.3
O2—C5—C6	121.8 (2)	C13—C14—C9	119.2 (2)
C4—C5—C6	117.2 (2)	C13—C14—H14	120.4
C5—C6—H6A	109.5	C9—C14—H14	120.4

C4—N1—N2—C7	−2.5 (3)	C4—C3—C7—C8	174.8 (3)
C4—N1—N2—C9	170.7 (2)	C2—C3—C7—C8	−3.5 (5)
O1—C2—C3—C7	11.2 (4)	N1—N2—C9—C10	57.7 (3)
C1—C2—C3—C7	−167.1 (3)	C7—N2—C9—C10	−130.3 (3)
O1—C2—C3—C4	−166.6 (3)	N1—N2—C9—C14	−121.2 (3)
C1—C2—C3—C4	15.0 (5)	C7—N2—C9—C14	50.9 (4)
N2—N1—C4—C3	1.4 (3)	C14—C9—C10—C11	−0.5 (4)
N2—N1—C4—C5	−175.3 (2)	N2—C9—C10—C11	−179.4 (2)
C7—C3—C4—N1	0.1 (3)	C9—C10—C11—C12	−0.6 (4)
C2—C3—C4—N1	178.3 (3)	C10—C11—C12—C13	1.4 (4)
C7—C3—C4—C5	175.9 (3)	C10—C11—C12—S1	−178.3 (2)
C2—C3—C4—C5	−6.0 (5)	O4—S1—C12—C11	−10.3 (3)
N1—C4—C5—O2	148.1 (3)	O3—S1—C12—C11	−139.6 (2)
C3—C4—C5—O2	−27.6 (5)	N3—S1—C12—C11	104.9 (2)
N1—C4—C5—C6	−29.0 (4)	O4—S1—C12—C13	169.9 (2)
C3—C4—C5—C6	155.3 (3)	O3—S1—C12—C13	40.7 (3)
N1—N2—C7—C3	2.7 (3)	N3—S1—C12—C13	−74.9 (2)
C9—N2—C7—C3	−169.8 (2)	C11—C12—C13—C14	−1.1 (4)
N1—N2—C7—C8	−174.3 (2)	S1—C12—C13—C14	178.6 (2)
C9—N2—C7—C8	13.2 (4)	C12—C13—C14—C9	0.0 (4)
C4—C3—C7—N2	−1.6 (3)	C10—C9—C14—C13	0.8 (4)
C2—C3—C7—N2	−179.9 (2)	N2—C9—C14—C13	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O2ⁱ	0.88 (1)	2.03 (1)	2.864 (3)	159 (3)
N3—H32···O4ⁱⁱ	0.88 (1)	2.06 (1)	2.933 (3)	170 (3)
C1—H1C···O3ⁱ	0.98	2.55	3.446 (3)	151
C10—H10···O1ⁱⁱⁱ	0.95	2.51	3.314 (3)	142
C14—H14···O1^iv	0.95	2.54	3.414 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₄S
M_r	321.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	8.3716 (3), 21.7722 (8), 7.8915 (3)
V (Å³)	1438.37 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.952, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10477, 3087, 2634
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.095, 1.05
No. of reflections	3087
No. of parameters	210
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)	0.31, −0.39
Absolute structure	Flack (1983), 1337 Friedel pairs
Absolute structure parameter	0.08 (8)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O2ⁱ	0.88 (1)	2.03 (1)	2.864 (3)	159 (3)
N3—H32···O4ⁱⁱ	0.88 (1)	2.06 (1)	2.933 (3)	170 (3)
C1—H1C···O3ⁱ	0.98	2.55	3.446 (3)	151
C10—H10···O1ⁱⁱⁱ	0.95	2.51	3.314 (3)	142
C14—H14···O1^iv	0.95	2.54	3.414 (3)	153

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

Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

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