3-(Di­phenyl­amino)­isobenzo­furan-1(3H)-one

Moreno-Fuquen, R.; Castillo, J.C.; Abonia, R.; Ellena, J.; Tenorio, J.C.

doi:10.1107/S1600536814006266

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o490

doi:10.1107/S1600536814006266

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3-(Diphenylamino)isobenzofuran-1(3H)-one

Rodolfo Moreno-Fuquen,^a ^* Juan C. Castillo,^a Rodrigo Abonia,^a Javier Ellena ^b and Juan C. Tenorio ^b

^aDepartamento de Química - Facultad de Ciencias Naturales y Exactas, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and ^bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 8 March 2014; accepted 20 March 2014; online 29 March 2014)

In the title isobenzofuranone derivative, C₂₀H₁₅NO₂, the planar fused-ring system (r.m.s. deviation for the 10 fitted atoms = 0.031 Å) forms dihedral angles of 63.58 (6) and 63.17 (8)° with the N-bound phenyl rings; the dihedral angle between the planes of these phenyl rings is 85.92 (7)°. In the crystal, molecules are linked by weak C—H⋯O interactions, involving both O atoms, forming helical supramolecular chains along [001].

CCDC reference: 992870

Related literature

For biological and pharmacological properties of isobenzofuranones, see: Anderson et al. (2005 ); Malpani et al. (2013 ); Shode et al. (2002 ); Yoganathan et al. (2003 ). For the synthesis of diverse amino derivatives, see: Abonia et al. (2010 , 2013 ); Moreno-Fuquen et al. (2013 ). For similar structures, see: Mendenhall et al. (2003 ); Reynolds & Scaringe (1982 ).

Experimental

Crystal data

C₂₀H₁₅NO₂
M_r = 301.33
Orthorhombic, P c a 2₁
a = 19.1440 (13) Å
b = 8.9363 (6) Å
c = 9.1111 (3) Å
V = 1558.70 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.56 × 0.37 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer
3011 measured reflections
1684 independent reflections
1366 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.09
1684 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.70	3.413 (3)	135
C1—H1⋯O1ⁱ	1.03 (3)	2.36 (3)	3.307 (3)	153 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 992870

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814006266/tk5299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006266/tk5299Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006266/tk5299Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

Reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co., and were used without additional purification. A 5 mL pyrex test tube was charged with a mixture of diphenylamine (102 mg, 0.60 mmol) and 2-formylbenzoic acid (90 mg, 0.60 mmol) without solvent. The mixture was heated in an oil bath at 120 °C for 1 h until the starting materials were not longer detected by thin-layer chromatography. The solid formed was removed and washed with cold ethanol (1 mL). White crystals of (I) were grown by slow evaporation, under ambient conditions, from its solution in ethanol [92% yield, M.p.: 396 (1) K].

Refinement top

All H-atoms, except H1, were positioned at geometrically idealized positions, C—H = 0.93 Å, and they were refined using a riding model approximation with U_iso(H) = 1.2U_eq(parent atom). Atom H1 was found from the Fourier difference map and its coordinates were freely refined. In the absence of significant anomalous scattering, Friedel pairs were merged.

Results and discussion top

Isobenzofuranones are an important class of synthetic and naturally occurring products exhibiting diverse biological and pharmacological properties. Some of them appear forming part of the structure of natural products such as fuscinarin (anti-HIV properties) (Yoganathan et al., 2003), typhaphthalide (phenolic compound isolated from Typha capensis) (Shode et al., 2002), noscapine (antitussive and anti-tumor properties) (Anderson et al., 2005), and synthetic compounds like some spirolactones (inhibitors of the influenza virus type B) (Malpani et al., 2013). Continuing with our current studies on the use of imines and imminium ions for the synthesis of diverse amino-derivatives of synthetic and biological interest (Abonia et al., 2010; Abonia et al., 2013; Moreno-Fuquen et al., 2013), 3-diphenylaminoisobenzofuran-1(3H)-one, (I), was obtained from the reaction of 2-formylbenzoic acid and diphenylamine through an imminium ion intermediate. The molecular structure of (I) is shown in Fig. 1. Taking the plane of the phthalide lactone C1—C8(=O1)—O2 (Mendenhall et al., 2003) as a point of reference, the title compound represents the first structure reported with ligands from C1. The bond lengths reported in the phthalide lactone (Reynolds & Scaringe, 1982) are very similar to those presented in (I). In the present molecule, rings A (C9—C14), B (C1—C8—O2) and C (C15—C20) are planar and show dihedral angles between them: A/B = 63.58 (6)°, C/B= 63.17 (8)° and A/C= 85.92 (7)°. In the crystal, the molecules are linked by weak C—H···O interactions, forming eight-membered {···HC₃H···OCO} synthons, leading to a chain along [001], Table 1 and Fig. 2.

Related literature top

For biological and pharmacological properties of isobenzofuranones, see: Anderson et al. (2005); Malpani et al. (2013); Shode et al. (2002); Yoganathan et al. (2003). For the synthesis of diverse amino derivatives, see: Abonia et al. (2010, 2013); Moreno-Fuquen et al. (2013). For similar structures, see: Mendenhall et al. (2003); Reynolds & Scaringe (1982).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. Molecular conformation and atom numbering scheme for (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I), showing the formation of helical chains running along [001]. Symmetry code: (i) -x+1/2, +y, +z-1/2.

3-(Diphenylamino)isobenzofuran-1(3H)-one top

Crystal data top

C₂₀H₁₅NO₂	D_x = 1.284 Mg m⁻³
M_r = 301.33	Melting point: 396(1) K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2966 reflections
a = 19.1440 (13) Å	θ = 3.1–26.4°
b = 8.9363 (6) Å	µ = 0.08 mm⁻¹
c = 9.1111 (3) Å	T = 295 K
V = 1558.70 (16) Å³	Block, white
Z = 4	0.56 × 0.37 × 0.19 mm
F(000) = 632

Data collection top

Nonius KappaCCD diffractometer	1366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 26.4°, θ_min = 3.1°
CCD rotation images, thick slices scans	h = −23→23
3011 measured reflections	k = −11→11
1684 independent reflections	l = −11→11

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0695P)² + 0.0242P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1684 reflections	Δρ_max = 0.15 e Å⁻³
213 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (9)

Crystal data top

C₂₀H₁₅NO₂	V = 1558.70 (16) Å³
M_r = 301.33	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 19.1440 (13) Å	µ = 0.08 mm⁻¹
b = 8.9363 (6) Å	T = 295 K
c = 9.1111 (3) Å	0.56 × 0.37 × 0.19 mm

Data collection top

Nonius KappaCCD diffractometer	1366 reflections with I > 2σ(I)
3011 measured reflections	R_int = 0.018
1684 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.15 e Å⁻³
1684 reflections	Δρ_min = −0.15 e Å⁻³
213 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.34995 (11)	1.2679 (2)	0.7466 (2)	0.0689 (6)
O2	0.29111 (9)	1.13804 (19)	0.5762 (2)	0.0578 (5)
N1	0.30495 (10)	0.9786 (2)	0.3646 (3)	0.0509 (5)
C1	0.28865 (13)	1.1262 (3)	0.4127 (3)	0.0517 (6)
C2	0.33858 (12)	1.2458 (3)	0.3647 (3)	0.0513 (6)
C3	0.35485 (15)	1.2966 (3)	0.2247 (3)	0.0580 (6)
H3	0.3353	1.2529	0.1417	0.070*
C4	0.40139 (16)	1.4151 (3)	0.2135 (4)	0.0672 (7)
H4	0.4129	1.4516	0.1210	0.081*
C5	0.43103 (17)	1.4803 (3)	0.3362 (4)	0.0761 (9)
H5	0.4626	1.5586	0.3248	0.091*
C6	0.41460 (15)	1.4311 (3)	0.4744 (4)	0.0705 (8)
H6	0.4343	1.4751	0.5572	0.085*
C7	0.36754 (13)	1.3130 (3)	0.4872 (3)	0.0549 (6)
C8	0.33827 (13)	1.2427 (3)	0.6184 (3)	0.0544 (6)
C9	0.37543 (12)	0.9290 (2)	0.3913 (3)	0.0487 (6)
C10	0.42604 (13)	0.9458 (3)	0.2845 (3)	0.0572 (6)
H10	0.4143	0.9877	0.1944	0.069*
C11	0.49369 (14)	0.9008 (3)	0.3103 (3)	0.0649 (7)
H11	0.5275	0.9128	0.2380	0.078*
C12	0.51118 (14)	0.8386 (3)	0.4422 (3)	0.0627 (7)
H12	0.5569	0.8083	0.4596	0.075*
C13	0.46114 (13)	0.8206 (3)	0.5498 (3)	0.0611 (6)
H13	0.4732	0.7782	0.6395	0.073*
C14	0.39338 (13)	0.8653 (3)	0.5245 (3)	0.0556 (7)
H14	0.3597	0.8526	0.5969	0.067*
C15	0.25151 (13)	0.8676 (2)	0.3667 (3)	0.0515 (6)
C16	0.26525 (14)	0.7304 (3)	0.3021 (4)	0.0699 (8)
H16	0.3089	0.7130	0.2607	0.084*
C17	0.21563 (16)	0.6196 (3)	0.2981 (5)	0.0791 (9)
H17	0.2261	0.5282	0.2547	0.095*
C18	0.15013 (16)	0.6429 (3)	0.3583 (4)	0.0710 (8)
H18	0.1167	0.5675	0.3569	0.085*
C19	0.13553 (17)	0.7796 (4)	0.4199 (4)	0.0743 (8)
H19	0.0912	0.7978	0.4576	0.089*
C20	0.18593 (15)	0.8909 (3)	0.4269 (3)	0.0663 (7)
H20	0.1757	0.9816	0.4721	0.080*
H1	0.2377 (16)	1.155 (3)	0.390 (3)	0.062 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0755 (12)	0.0675 (12)	0.0638 (13)	0.0031 (9)	−0.0014 (9)	−0.0069 (9)
O2	0.0599 (11)	0.0522 (10)	0.0612 (11)	−0.0026 (8)	0.0074 (8)	−0.0047 (8)
N1	0.0455 (10)	0.0432 (10)	0.0639 (11)	−0.0007 (8)	−0.0019 (9)	−0.0033 (9)
C1	0.0475 (15)	0.0471 (14)	0.0606 (15)	0.0006 (10)	0.0022 (10)	0.0001 (11)
C2	0.0478 (13)	0.0414 (12)	0.0647 (15)	0.0025 (9)	0.0014 (11)	−0.0001 (11)
C3	0.0596 (15)	0.0501 (15)	0.0644 (16)	0.0045 (12)	0.0002 (11)	0.0004 (12)
C4	0.0746 (17)	0.0537 (15)	0.0734 (18)	−0.0006 (13)	0.0104 (14)	0.0085 (14)
C5	0.083 (2)	0.0531 (15)	0.093 (2)	−0.0173 (14)	0.0150 (16)	−0.0035 (15)
C6	0.0754 (18)	0.0539 (15)	0.082 (2)	−0.0149 (14)	0.0009 (16)	−0.0087 (14)
C7	0.0539 (13)	0.0439 (13)	0.0669 (14)	0.0031 (11)	0.0010 (12)	−0.0045 (12)
C8	0.0522 (13)	0.0489 (14)	0.0623 (16)	0.0059 (11)	0.0001 (11)	−0.0064 (12)
C9	0.0484 (13)	0.0420 (12)	0.0556 (14)	−0.0046 (10)	0.0000 (10)	−0.0038 (10)
C10	0.0593 (14)	0.0572 (14)	0.0550 (13)	0.0032 (12)	0.0052 (12)	0.0058 (12)
C11	0.0542 (15)	0.0651 (16)	0.0755 (17)	0.0043 (12)	0.0137 (13)	0.0084 (14)
C12	0.0505 (14)	0.0598 (15)	0.0777 (18)	0.0022 (12)	−0.0056 (12)	−0.0021 (13)
C13	0.0650 (16)	0.0601 (15)	0.0581 (14)	0.0026 (13)	−0.0091 (13)	−0.0005 (13)
C14	0.0578 (15)	0.0550 (15)	0.0539 (16)	−0.0006 (12)	0.0014 (11)	−0.0014 (10)
C15	0.0529 (13)	0.0477 (12)	0.0540 (12)	−0.0047 (11)	−0.0036 (11)	0.0012 (10)
C16	0.0576 (16)	0.0536 (14)	0.098 (2)	−0.0017 (12)	−0.0010 (15)	−0.0138 (16)
C17	0.074 (2)	0.0509 (15)	0.112 (3)	−0.0070 (13)	−0.0064 (18)	−0.0137 (18)
C18	0.076 (2)	0.0639 (17)	0.0731 (17)	−0.0251 (14)	−0.0109 (15)	0.0048 (15)
C19	0.0645 (16)	0.087 (2)	0.0717 (17)	−0.0225 (15)	0.0127 (14)	−0.0074 (16)
C20	0.0624 (17)	0.0656 (16)	0.0709 (16)	−0.0131 (13)	0.0122 (13)	−0.0122 (14)

Geometric parameters (Å, º) top

O1—C8	1.210 (4)	C10—C11	1.376 (4)
O2—C8	1.355 (3)	C10—H10	0.9300
O2—C1	1.494 (3)	C11—C12	1.366 (4)
N1—C15	1.425 (3)	C11—H11	0.9300
N1—C1	1.425 (3)	C12—C13	1.380 (4)
N1—C9	1.441 (3)	C12—H12	0.9300
C1—C2	1.499 (3)	C13—C14	1.377 (4)
C1—H1	1.03 (3)	C13—H13	0.9300
C2—C7	1.383 (4)	C14—H14	0.9300
C2—C3	1.389 (4)	C15—C16	1.385 (4)
C3—C4	1.388 (4)	C15—C20	1.386 (4)
C3—H3	0.9300	C16—C17	1.372 (4)
C4—C5	1.383 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.384 (5)
C5—C6	1.371 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.373 (5)
C6—C7	1.392 (4)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.387 (4)
C7—C8	1.462 (4)	C19—H19	0.9300
C9—C10	1.382 (3)	C20—H20	0.9300
C9—C14	1.384 (3)

C8—O2—C1	110.6 (2)	C11—C10—C9	120.5 (3)
C15—N1—C1	118.89 (19)	C11—C10—H10	119.8
C15—N1—C9	117.15 (18)	C9—C10—H10	119.8
C1—N1—C9	115.92 (19)	C12—C11—C10	120.0 (2)
N1—C1—O2	111.4 (2)	C12—C11—H11	120.0
N1—C1—C2	115.5 (2)	C10—C11—H11	120.0
O2—C1—C2	102.75 (19)	C11—C12—C13	120.2 (2)
N1—C1—H1	112.2 (15)	C11—C12—H12	119.9
O2—C1—H1	102.2 (17)	C13—C12—H12	119.9
C2—C1—H1	111.6 (15)	C14—C13—C12	120.1 (3)
C7—C2—C3	120.6 (2)	C14—C13—H13	120.0
C7—C2—C1	109.2 (2)	C12—C13—H13	120.0
C3—C2—C1	130.1 (2)	C13—C14—C9	120.0 (2)
C4—C3—C2	117.5 (3)	C13—C14—H14	120.0
C4—C3—H3	121.3	C9—C14—H14	120.0
C2—C3—H3	121.3	C16—C15—C20	118.3 (2)
C5—C4—C3	121.7 (3)	C16—C15—N1	118.3 (2)
C5—C4—H4	119.2	C20—C15—N1	123.4 (2)
C3—C4—H4	119.2	C17—C16—C15	121.2 (3)
C6—C5—C4	120.9 (3)	C17—C16—H16	119.4
C6—C5—H5	119.5	C15—C16—H16	119.4
C4—C5—H5	119.5	C16—C17—C18	120.6 (3)
C5—C6—C7	117.9 (3)	C16—C17—H17	119.7
C5—C6—H6	121.0	C18—C17—H17	119.7
C7—C6—H6	121.0	C19—C18—C17	118.7 (3)
C2—C7—C6	121.4 (3)	C19—C18—H18	120.7
C2—C7—C8	108.6 (2)	C17—C18—H18	120.7
C6—C7—C8	129.9 (3)	C18—C19—C20	121.0 (3)
O1—C8—O2	121.7 (2)	C18—C19—H19	119.5
O1—C8—C7	129.6 (2)	C20—C19—H19	119.5
O2—C8—C7	108.6 (2)	C19—C20—C15	120.3 (3)
C10—C9—C14	119.2 (2)	C19—C20—H20	119.9
C10—C9—N1	120.3 (2)	C15—C20—H20	119.9
C14—C9—N1	120.5 (2)

C15—N1—C1—O2	81.6 (3)	C6—C7—C8—O2	176.1 (3)
C9—N1—C1—O2	−66.3 (3)	C15—N1—C9—C10	117.8 (2)
C15—N1—C1—C2	−161.6 (2)	C1—N1—C9—C10	−93.7 (3)
C9—N1—C1—C2	50.4 (3)	C15—N1—C9—C14	−62.7 (3)
C8—O2—C1—N1	121.2 (2)	C1—N1—C9—C14	85.9 (3)
C8—O2—C1—C2	−3.1 (3)	C14—C9—C10—C11	−0.6 (4)
N1—C1—C2—C7	−119.6 (2)	N1—C9—C10—C11	179.0 (2)
O2—C1—C2—C7	2.0 (3)	C9—C10—C11—C12	0.2 (4)
N1—C1—C2—C3	63.7 (4)	C10—C11—C12—C13	0.0 (4)
O2—C1—C2—C3	−174.8 (3)	C11—C12—C13—C14	0.0 (4)
C7—C2—C3—C4	0.7 (4)	C12—C13—C14—C9	−0.3 (4)
C1—C2—C3—C4	177.1 (3)	C10—C9—C14—C13	0.6 (4)
C2—C3—C4—C5	0.4 (4)	N1—C9—C14—C13	−178.9 (2)
C3—C4—C5—C6	−0.9 (5)	C1—N1—C15—C16	171.7 (3)
C4—C5—C6—C7	0.4 (5)	C9—N1—C15—C16	−40.7 (3)
C3—C2—C7—C6	−1.2 (4)	C1—N1—C15—C20	−6.7 (4)
C1—C2—C7—C6	−178.3 (2)	C9—N1—C15—C20	140.9 (3)
C3—C2—C7—C8	176.8 (2)	C20—C15—C16—C17	−0.4 (5)
C1—C2—C7—C8	−0.3 (3)	N1—C15—C16—C17	−178.8 (3)
C5—C6—C7—C2	0.7 (4)	C15—C16—C17—C18	0.4 (5)
C5—C6—C7—C8	−176.9 (3)	C16—C17—C18—C19	1.0 (5)
C1—O2—C8—O1	−178.2 (2)	C17—C18—C19—C20	−2.3 (5)
C1—O2—C8—C7	3.0 (3)	C18—C19—C20—C15	2.3 (5)
C2—C7—C8—O1	179.6 (3)	C16—C15—C20—C19	−0.9 (4)
C6—C7—C8—O1	−2.6 (5)	N1—C15—C20—C19	177.5 (3)
C2—C7—C8—O2	−1.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.70	3.413 (3)	135
C1—H1···O1ⁱ	1.03 (3)	2.36 (3)	3.307 (3)	153 (2)

Symmetry code: (i) −x+1/2, y, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.70	3.413 (3)	135
C1—H1···O1ⁱ	1.03 (3)	2.36 (3)	3.307 (3)	153 (2)

Symmetry code: (i) −x+1/2, y, z−1/2.

Acknowledgements

RMF and RA are grateful to the Universidad del Valle, Colombia, for partial financial support. JCC acknowledges his doctoral fellowship granted by COLCIENCIAS.

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