organic compounds
3-(Diphenylamino)isobenzofuran-1(3H)-one
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
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
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Data collection: COLLECT (Nonius, 2000); cell 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
10.1107/S1600536814006266/tk5299sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006266/tk5299Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006266/tk5299Isup3.cml
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
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].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 Uiso(H) = 1.2Ueq(parent atom). Atom H1 was found from the Fourier difference map and its coordinates were freely refined. In the absence of significant
Friedel pairs were merged.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
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.Data collection: COLLECT (Nonius, 2000); cell
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).C20H15NO2 | Dx = 1.284 Mg m−3 |
Mr = 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 |
Nonius KappaCCD diffractometer | 1366 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 26.4°, θmin = 3.1° |
CCD rotation images, thick slices scans | h = −23→23 |
3011 measured reflections | k = −11→11 |
1684 independent reflections | l = −11→11 |
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(Fo2) + (0.0695P)2 + 0.0242P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1684 reflections | Δρmax = 0.15 e Å−3 |
213 parameters | Δρmin = −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) |
C20H15NO2 | V = 1558.70 (16) Å3 |
Mr = 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 |
Nonius KappaCCD diffractometer | 1366 reflections with I > 2σ(I) |
3011 measured reflections | Rint = 0.018 |
1684 independent reflections |
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 | Δρmax = 0.15 e Å−3 |
1684 reflections | Δρmin = −0.15 e Å−3 |
213 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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. |
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.
References
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