3-(Di-phenyl-amino)-isobenzo-furan-1(3H)-one.

In the title isobenzo-furan-one 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, mol-ecules are linked by weak C-H⋯O inter-actions, involving both O atoms, forming helical supra-molecular chains along [001].

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 = 301.33

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.09

1684 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006266/tk5299sup1.cif

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

Click here for additional data file.

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

CCDC reference: 992870

Additional supporting information: crystallographic information; 3D view; checkCIF report

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)

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)

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) .