(2S,4R,5S)-5-Allyl-4-hydroxy­tetra­hydro-2-furylmethyl p-toluene­sulfonate

Paz-Morales, E.; Sartillo-Piscil, F.; Mendoza, A.

doi:10.1107/S160053680902011X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1456

doi:10.1107/S160053680902011X

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(2S,4R,5S)-5-Allyl-4-hydroxytetrahydro-2-furylmethyl p-toluenesulfonate

Evelyn Paz-Morales,^a Fernando Sartillo-Piscil ^a and Angel Mendoza ^b ^*

^aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico, and ^bCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico
^*Correspondence e-mail: angel.mendoza.m@gmail.com

(Received 8 May 2009; accepted 26 May 2009; online 6 June 2009)

In the title compound, C₁₅H₂₀O₅S, the tetrahydrofuran ring shows an envelope conformation. The crystal packing is stabilized by an intermolecular O—H⋯O hydrogen bond, generating a ribbon structure along the a axis. Two weak intermolecular C—H⋯O interactions are also observed.

Related literature

For the synthesis of chiral tetrahydrofurans bearing an allyl group at the C1 position, see: Romero et al. (2006 ); Sartillo-Melendez et al. (2006 ); Hernández-Garcia et al. (2009 ); Paz-Morales et al. (2009 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₂₀O₅S
M_r = 312.37
Monoclinic, P 2₁
a = 5.9420 (12) Å
b = 16.966 (3) Å
c = 8.1980 (19) Å
β = 100.09 (2)°
V = 813.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.6 × 0.4 × 0.3 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
2127 measured reflections
1575 independent reflections
1099 reflections with I > 2σ(I)
R_int = 0.030
3 standard reflections every 97 reflections intensity decay: 7%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.126
S = 1.07
1575 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 97 Friedel pairs
Flack parameter: −0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5O⋯O1ⁱ	0.96 (11)	1.83 (11)	2.782 (7)	171 (10)
C5—H5B⋯O4ⁱ	0.97	2.49	3.188 (8)	129
C13—H13⋯O3ⁱⁱ	0.93	2.46	3.350 (8)	161
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1.

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); 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/S160053680902011X/is2418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902011X/is2418Isup2.hkl

checkCIF report

Comment top

During the course of our investigations led to the synthesis of chiral tetrahydrofurans bearing an allyl group at C1 position (Romero et al., 2006; Sartillo-Melendez et al., 2006; Hernández-Garcia et al., 2009; Paz-Morales et al., 2009), the title compound was obtained and separated by crystallization from the its C1-epimer.

In the crystal structure, the tosyl ring and terminal double bond reach a close distance from each one (C7···C13 and C8···C12 = ca. 3.9 Å), with allyl π orbital being perpendicular for those of the aromatic ring. The furane ring (O1/C1–C4) shows an envelope conformation on atom C2 with puckering parameters (Cremer & Pople, 1975) q₂ = 0.348 (8) Å and ϕ₂ = 72.3 (12)°. The molecules are linked by hydrogen bond [O1···O5 = 2.782 (7) Å] interactions, building a ribbon structure along the [100] direction.

Related literature top

For the synthesis of chiral tetrahydrofurans bearing an allyl group at C1 positio, see: Romero et al. (2006); Sartillo-Melendez et al. (2006); Hernández-Garcia et al. (2009); Paz-Morales et al. (2009). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained from a solution of 1,2-O-isopropylidene-α-D-xylofuranose derivative (1.0 mmol) in 10 ml of dry CH₂Cl₂. This was treated with allyltrimethylsilane (6.0 mmol) at room temperature over 10 min and the reaction mixture was cooled at 0 °C, then BF₃OEt₂ (6.0 mmol) was added dropwise. The reaction mixture was warmed at room temperature over 6 hrs and was treated with saturated aqueous solution of NaHCO₃ (10 ml). The aqueous layer was extracted three times with CH₂Cl₂ (20 ml). The organic phase was dried with MgSO₄, concentrated and purified by flash chromatography on silica gel (hexane: ethyl acetate). The absolute configuration was established by the structure determination of 1,2-O-isopropylidene-α-D-xylofuranose of known absolute configuration of starting material.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SIR2004 (Burla et al., 2005); 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

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, showing molecules connected by O5—H···O1ⁱ hydrogen bonds and intermolecular weak interactions (dashed lines).

(2S,4R,5S)-5-Allyl-4-hydroxytetrahydro-2-furylmethyl p-toluenesulfonate top

Crystal data top

C₁₅H₂₀O₅S	F(000) = 332
M_r = 312.37	D_x = 1.275 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 40 reflections
a = 5.9420 (12) Å	θ = 4.8–24.7°
b = 16.966 (3) Å	µ = 0.22 mm⁻¹
c = 8.1980 (19) Å	T = 293 K
β = 100.09 (2)°	Prism, colorless
V = 813.7 (3) Å³	0.6 × 0.4 × 0.3 mm
Z = 2

Data collection top

Bruker P4 diffractometer	R_int = 0.030
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.4°
Graphite monochromator	h = −1→7
2θ/ω scans	k = −1→20
2127 measured reflections	l = −9→9
1575 independent reflections	3 standard reflections every 97 reflections
1099 reflections with I > 2σ(I)	intensity decay: 7%

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0261P)² + 0.5527P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1575 reflections	Δρ_max = 0.26 e Å⁻³
194 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 97 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (2)

Crystal data top

C₁₅H₂₀O₅S	V = 813.7 (3) Å³
M_r = 312.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.9420 (12) Å	µ = 0.22 mm⁻¹
b = 16.966 (3) Å	T = 293 K
c = 8.1980 (19) Å	0.6 × 0.4 × 0.3 mm
β = 100.09 (2)°

Data collection top

Bruker P4 diffractometer	R_int = 0.030
2127 measured reflections	3 standard reflections every 97 reflections
1575 independent reflections	intensity decay: 7%
1099 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	Δρ_max = 0.26 e Å⁻³
S = 1.07	Δρ_min = −0.23 e Å⁻³
1575 reflections	Absolute structure: Flack (1983), 97 Friedel pairs
194 parameters	Absolute structure parameter: −0.1 (2)
1 restraint

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 > 2σ(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
S1	0.2153 (3)	0.44181 (11)	0.35980 (19)	0.0535 (4)
O4	−0.0229 (6)	0.4463 (4)	0.3656 (5)	0.0664 (12)
O2	0.2892 (7)	0.5318 (3)	0.3599 (6)	0.0586 (12)
C9	0.3645 (10)	0.4054 (4)	0.5478 (7)	0.0456 (14)
O1	0.5274 (7)	0.6525 (3)	0.5384 (7)	0.0707 (15)
O3	0.2936 (8)	0.4018 (3)	0.2256 (5)	0.0673 (14)
O5	1.1076 (9)	0.7133 (4)	0.5830 (9)	0.092 (2)
C10	0.5693 (10)	0.3653 (4)	0.5528 (8)	0.0488 (15)
H10	0.6287	0.3575	0.4564	0.059*
C4	0.5632 (11)	0.6353 (4)	0.3722 (9)	0.0615 (19)
H4	0.4558	0.6660	0.2926	0.074*
C11	0.6847 (12)	0.3367 (4)	0.7038 (9)	0.0611 (19)
H11	0.8222	0.3100	0.7077	0.073*
C14	0.2741 (12)	0.4168 (4)	0.6894 (8)	0.0614 (19)
H14	0.1377	0.4441	0.6860	0.074*
C2	0.9228 (11)	0.6608 (4)	0.5423 (10)	0.065 (2)
H2	0.9719	0.6073	0.5770	0.077*
C5	0.5240 (11)	0.5496 (4)	0.3390 (9)	0.0626 (19)
H5A	0.5446	0.5370	0.2271	0.075*
H5B	0.6317	0.5186	0.4158	0.075*
C3	0.8076 (12)	0.6601 (5)	0.3629 (10)	0.075 (2)
H3A	0.8799	0.6225	0.2994	0.090*
H3B	0.8110	0.7119	0.3135	0.090*
C13	0.3905 (13)	0.3868 (5)	0.8364 (9)	0.070 (2)
H13	0.3274	0.3931	0.9317	0.084*
C12	0.5976 (12)	0.3476 (5)	0.8486 (8)	0.065 (2)
C1	0.7298 (11)	0.6868 (5)	0.6323 (10)	0.068 (2)
H1	0.7159	0.7442	0.6244	0.082*
C15	0.7242 (14)	0.3163 (6)	1.0118 (9)	0.092 (3)
H15A	0.7423	0.2603	1.0040	0.138*
H15B	0.6388	0.3280	1.0980	0.138*
H15C	0.8719	0.3408	1.0370	0.138*
C7	0.765 (2)	0.5786 (7)	0.8486 (12)	0.100 (3)
H7	0.6437	0.5466	0.8007	0.120*
C6	0.7504 (16)	0.6637 (5)	0.8113 (11)	0.088 (3)
H6A	0.8857	0.6888	0.8728	0.106*
H6B	0.6196	0.6849	0.8526	0.106*
C8	0.938 (2)	0.5455 (8)	0.9454 (12)	0.135 (5)
H8A	1.0609	0.5760	0.9949	0.162*
H8B	0.9375	0.4915	0.9645	0.162*
H5O	1.26 (2)	0.695 (7)	0.578 (14)	0.162*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0460 (8)	0.0574 (9)	0.0559 (9)	−0.0012 (9)	0.0053 (7)	0.0015 (10)
O4	0.038 (2)	0.080 (3)	0.081 (3)	−0.001 (3)	0.010 (2)	0.008 (4)
O2	0.044 (2)	0.050 (3)	0.084 (3)	−0.003 (2)	0.017 (2)	0.008 (2)
C9	0.046 (3)	0.043 (3)	0.048 (3)	−0.006 (3)	0.008 (3)	0.002 (3)
O1	0.035 (2)	0.087 (4)	0.093 (4)	−0.009 (3)	0.020 (2)	−0.010 (3)
O3	0.078 (3)	0.079 (3)	0.046 (2)	−0.003 (3)	0.013 (2)	−0.015 (2)
O5	0.050 (3)	0.082 (4)	0.146 (5)	−0.010 (3)	0.022 (4)	−0.015 (4)
C10	0.042 (4)	0.052 (4)	0.054 (4)	−0.004 (3)	0.013 (3)	−0.005 (3)
C4	0.049 (4)	0.052 (4)	0.082 (5)	0.005 (3)	0.009 (4)	0.016 (4)
C11	0.053 (4)	0.059 (5)	0.068 (4)	0.008 (4)	0.000 (3)	0.009 (4)
C14	0.062 (4)	0.073 (5)	0.051 (4)	0.010 (4)	0.013 (3)	−0.006 (3)
C2	0.033 (3)	0.051 (4)	0.109 (6)	−0.001 (3)	0.012 (4)	0.001 (4)
C5	0.048 (4)	0.061 (4)	0.083 (5)	0.004 (4)	0.021 (4)	0.012 (4)
C3	0.056 (4)	0.072 (5)	0.102 (6)	−0.012 (4)	0.028 (4)	0.018 (5)
C13	0.068 (5)	0.089 (6)	0.055 (4)	0.007 (4)	0.017 (4)	−0.007 (4)
C12	0.062 (5)	0.072 (5)	0.057 (4)	−0.013 (4)	0.000 (3)	−0.001 (4)
C1	0.041 (4)	0.061 (5)	0.104 (6)	0.007 (3)	0.017 (4)	0.003 (4)
C15	0.091 (6)	0.109 (7)	0.066 (5)	−0.001 (6)	−0.010 (4)	0.028 (5)
C7	0.117 (9)	0.100 (8)	0.080 (6)	−0.020 (7)	0.014 (6)	−0.011 (6)
C6	0.076 (6)	0.083 (7)	0.108 (7)	−0.011 (5)	0.022 (5)	−0.017 (6)
C8	0.181 (12)	0.135 (10)	0.088 (7)	0.042 (10)	0.023 (8)	0.016 (7)

Geometric parameters (Å, º) top

S1—O4	1.427 (4)	C2—C1	1.533 (9)
S1—O3	1.437 (5)	C2—H2	0.9800
S1—O2	1.589 (5)	C5—H5A	0.9700
S1—C9	1.751 (6)	C5—H5B	0.9700
O2—C5	1.467 (7)	C3—H3A	0.9700
C9—C14	1.375 (8)	C3—H3B	0.9700
C9—C10	1.389 (8)	C13—C12	1.386 (10)
O1—C1	1.433 (8)	C13—H13	0.9300
O1—C4	1.445 (8)	C12—C15	1.512 (9)
O5—C2	1.408 (8)	C1—C6	1.503 (11)
O5—H5O	0.96 (11)	C1—H1	0.9800
C10—C11	1.392 (9)	C15—H15A	0.9600
C10—H10	0.9300	C15—H15B	0.9600
C4—C5	1.490 (10)	C15—H15C	0.9600
C4—C3	1.526 (9)	C7—C8	1.311 (14)
C4—H4	0.9800	C7—C6	1.475 (13)
C11—C12	1.388 (9)	C7—H7	0.9300
C11—H11	0.9300	C6—H6A	0.9700
C14—C13	1.378 (9)	C6—H6B	0.9700
C14—H14	0.9300	C8—H8A	0.9300
C2—C3	1.509 (10)	C8—H8B	0.9300

O4—S1—O3	120.5 (3)	H5A—C5—H5B	108.5
O4—S1—O2	103.0 (3)	C2—C3—C4	103.1 (6)
O3—S1—O2	109.1 (3)	C2—C3—H3A	111.1
O4—S1—C9	110.0 (3)	C4—C3—H3A	111.1
O3—S1—C9	109.0 (3)	C2—C3—H3B	111.1
O2—S1—C9	104.0 (3)	C4—C3—H3B	111.1
C5—O2—S1	117.7 (4)	H3A—C3—H3B	109.1
C14—C9—C10	120.9 (6)	C14—C13—C12	122.9 (7)
C14—C9—S1	118.7 (5)	C14—C13—H13	118.6
C10—C9—S1	120.3 (5)	C12—C13—H13	118.6
C1—O1—C4	109.9 (5)	C13—C12—C11	117.5 (6)
C2—O5—H5O	119 (7)	C13—C12—C15	122.0 (7)
C9—C10—C11	119.3 (6)	C11—C12—C15	120.5 (7)
C9—C10—H10	120.4	O1—C1—C6	109.6 (6)
C11—C10—H10	120.4	O1—C1—C2	104.6 (6)
O1—C4—C5	109.0 (6)	C6—C1—C2	117.1 (7)
O1—C4—C3	106.9 (6)	O1—C1—H1	108.4
C5—C4—C3	112.3 (6)	C6—C1—H1	108.4
O1—C4—H4	109.6	C2—C1—H1	108.4
C5—C4—H4	109.6	C12—C15—H15A	109.5
C3—C4—H4	109.6	C12—C15—H15B	109.5
C12—C11—C10	121.0 (7)	H15A—C15—H15B	109.5
C12—C11—H11	119.5	C12—C15—H15C	109.5
C10—C11—H11	119.5	H15A—C15—H15C	109.5
C9—C14—C13	118.4 (6)	H15B—C15—H15C	109.5
C9—C14—H14	120.8	C8—C7—C6	123.7 (12)
C13—C14—H14	120.8	C8—C7—H7	118.1
O5—C2—C3	116.0 (7)	C6—C7—H7	118.1
O5—C2—C1	108.8 (6)	C7—C6—C1	116.7 (8)
C3—C2—C1	102.8 (6)	C7—C6—H6A	108.1
O5—C2—H2	109.7	C1—C6—H6A	108.1
C3—C2—H2	109.7	C7—C6—H6B	108.1
C1—C2—H2	109.7	C1—C6—H6B	108.1
O2—C5—C4	107.5 (5)	H6A—C6—H6B	107.3
O2—C5—H5A	110.2	C7—C8—H8A	120.0
C4—C5—H5A	110.2	C7—C8—H8B	120.0
O2—C5—H5B	110.2	H8A—C8—H8B	120.0
C4—C5—H5B	110.2

O4—S1—O2—C5	−174.5 (5)	O5—C2—C3—C4	−151.9 (6)
O3—S1—O2—C5	−45.4 (5)	C1—C2—C3—C4	−33.3 (8)
C9—S1—O2—C5	70.8 (5)	O1—C4—C3—C2	21.1 (8)
O4—S1—C9—C14	−26.7 (6)	C5—C4—C3—C2	−98.3 (8)
O3—S1—C9—C14	−160.7 (5)	C9—C14—C13—C12	1.9 (12)
O2—S1—C9—C14	83.0 (6)	C14—C13—C12—C11	−2.0 (12)
O4—S1—C9—C10	152.9 (5)	C14—C13—C12—C15	179.0 (8)
O3—S1—C9—C10	18.9 (6)	C10—C11—C12—C13	0.9 (11)
O2—S1—C9—C10	−97.4 (5)	C10—C11—C12—C15	179.9 (7)
C14—C9—C10—C11	−0.4 (9)	C4—O1—C1—C6	−148.3 (6)
S1—C9—C10—C11	−179.9 (5)	C4—O1—C1—C2	−21.9 (8)
C1—O1—C4—C5	122.2 (6)	O5—C2—C1—O1	158.0 (6)
C1—O1—C4—C3	0.6 (8)	C3—C2—C1—O1	34.5 (8)
C9—C10—C11—C12	0.2 (10)	O5—C2—C1—C6	−80.5 (9)
C10—C9—C14—C13	−0.6 (10)	C3—C2—C1—C6	156.1 (7)
S1—C9—C14—C13	178.9 (6)	C8—C7—C6—C1	120.2 (11)
S1—O2—C5—C4	−170.4 (5)	O1—C1—C6—C7	59.6 (11)
O1—C4—C5—O2	58.8 (7)	C2—C1—C6—C7	−59.3 (12)
C3—C4—C5—O2	177.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O1ⁱ	0.96 (11)	1.83 (11)	2.782 (7)	171 (10)
C5—H5B···O4ⁱ	0.97	2.49	3.188 (8)	129
C13—H13···O3ⁱⁱ	0.93	2.46	3.350 (8)	161

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀O₅S
M_r	312.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.9420 (12), 16.966 (3), 8.1980 (19)
β (°)	100.09 (2)
V (Å³)	813.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.6 × 0.4 × 0.3

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2127, 1575, 1099
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.126, 1.07
No. of reflections	1575
No. of parameters	194
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23
Absolute structure	Flack (1983), 97 Friedel pairs
Absolute structure parameter	−0.1 (2)

Computer programs: XSCANS (Siemens, 1994), SIR2004 (Burla et al., 2005), 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
O5—H5O···O1ⁱ	0.96 (11)	1.83 (11)	2.782 (7)	171 (10)
C5—H5B···O4ⁱ	0.97	2.49	3.188 (8)	129
C13—H13···O3ⁱⁱ	0.93	2.46	3.350 (8)	161

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

Acknowledgements

We gratefully acknowledge financial support from CONACYT (grant No. 62203 and Graduate Scholarship 159362) and Facultad de Ciencias Químicas (BUAP).

References

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