2-(4-Hydroxy-biphenyl-3-yl)isoindolin-1-one.

In the mol-ecular structure of the title compound, C(20)H(15)NO(2), the isoindolin-1-one unit is planar, the maximum atomic deviation being 0.048 (2) Å. The two biphenyl rings are twisted with respect to the isoindolin-1-one plane, making dihedral angles of 33.21 (9) and 33.34 (9)°. The two benzene rings of the biphenyl substituent are oriented at a dihedral angle of 35.43 (11)° to each other. An intra-molecular O-H⋯O inter-action occurs and inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the biological activity of isoindolin-1-ones, see: Nozawa et al. (1997 ▶); Atack et al. (2006 ▶); Lunn et al. (2004 ▶). For the reaction conditions for the synthesis of the title compound, see: Wu et al. (2007 ▶). For the palladium-catalysed intra­molecular deca­rbonylative coupling mechanism, see: Baudoin (2007 ▶).

Experimental

Crystal data

C20H15NO2

M = 301.33

Tetragonal,

a = 7.5123 (2) Å

c = 52.3543 (17) Å

V = 2954.60 (15) Å3

Z = 8

Cu Kα radiation

μ = 0.70 mm−1

T = 294 K

0.32 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.822, T max = 0.900

10482 measured reflections

1676 independent reflections

1556 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.08

1676 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002370/xu2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002370/xu2719Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H15NO2	Dx = 1.355 Mg m−3
Mr = 301.33	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P43212	Cell parameters from 3246 reflections
Hall symbol: P 4nw 2abw	θ = 3.5–65.0°
a = 7.5123 (2) Å	µ = 0.70 mm−1
c = 52.3543 (17) Å	T = 294 K
V = 2954.60 (15) Å3	Prism, colorless
Z = 8	0.32 × 0.22 × 0.20 mm
F(000) = 1264

Rigaku R-AXIS RAPID IP diffractometer	1676 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 67.1°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→8
Tmin = 0.822, Tmax = 0.900	l = −56→61
10482 measured reflections

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.7354P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1676 reflections	Δρmax = 0.16 e Å−3
210 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00108 (16)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	1.19213 (19)	0.1923 (2)	0.94864 (3)	0.0332 (4)
O2	1.2708 (2)	−0.0751 (2)	0.92001 (2)	0.0343 (4)
H2	1.2642	0.0021	0.9310	0.052*
N1	0.9322 (2)	0.1133 (2)	0.92751 (3)	0.0227 (4)
C1	0.6483 (3)	0.0856 (3)	0.83609 (4)	0.0298 (5)
H1	0.5924	0.0596	0.8515	0.036*
C2	0.5463 (3)	0.1296 (3)	0.81496 (4)	0.0349 (5)
H2A	0.4229	0.1325	0.8163	0.042*
C3	0.6272 (3)	0.1694 (3)	0.79190 (4)	0.0348 (5)
H3	0.5589	0.2004	0.7778	0.042*
C4	0.8105 (3)	0.1625 (3)	0.79011 (3)	0.0326 (5)
H4	0.8655	0.1875	0.7746	0.039*
C5	0.9131 (3)	0.1186 (3)	0.81118 (3)	0.0282 (5)
H5	1.0364	0.1150	0.8097	0.034*
C6	0.8337 (3)	0.0797 (3)	0.83461 (3)	0.0239 (4)
C7	0.9453 (3)	0.0361 (3)	0.85723 (3)	0.0242 (4)
C8	1.1044 (3)	−0.0590 (3)	0.85490 (3)	0.0282 (5)
H8	1.1399	−0.1008	0.8390	0.034*
C9	1.2093 (3)	−0.0914 (3)	0.87605 (4)	0.0297 (5)
H9	1.3153	−0.1539	0.8741	0.036*
C10	1.1605 (3)	−0.0328 (3)	0.90024 (3)	0.0266 (5)
C11	0.9992 (3)	0.0590 (3)	0.90309 (3)	0.0232 (4)
C12	0.8957 (3)	0.0937 (3)	0.88161 (3)	0.0231 (4)
H12	0.7902	0.1572	0.8835	0.028*
C13	1.0282 (3)	0.1716 (3)	0.94795 (3)	0.0252 (4)
C14	0.7394 (3)	0.1129 (3)	0.93267 (3)	0.0232 (4)
H14A	0.6893	−0.0053	0.9306	0.028*
H14B	0.6770	0.1950	0.9215	0.028*
C15	0.7311 (3)	0.1730 (3)	0.96011 (3)	0.0224 (4)
C16	0.9020 (3)	0.2040 (3)	0.96878 (3)	0.0236 (4)
C17	0.9354 (3)	0.2596 (3)	0.99368 (3)	0.0282 (5)
H17	1.0510	0.2791	0.9994	0.034*
C18	0.7913 (3)	0.2848 (3)	1.00959 (3)	0.0295 (5)
H18	0.8097	0.3196	1.0264	0.035*
C19	0.6183 (3)	0.2586 (3)	1.00072 (4)	0.0289 (5)
H19	0.5228	0.2788	1.0116	0.035*
C20	0.5861 (3)	0.2026 (3)	0.97573 (3)	0.0272 (4)
H20	0.4706	0.1857	0.9698	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0203 (8)	0.0453 (10)	0.0340 (7)	−0.0038 (7)	−0.0027 (6)	−0.0023 (7)
O2	0.0300 (8)	0.0425 (10)	0.0305 (7)	0.0109 (7)	−0.0058 (6)	0.0042 (6)
N1	0.0195 (8)	0.0270 (9)	0.0216 (7)	−0.0004 (7)	−0.0002 (6)	0.0013 (6)
C1	0.0282 (11)	0.0328 (12)	0.0283 (9)	−0.0004 (9)	0.0017 (8)	−0.0037 (9)
C2	0.0233 (11)	0.0391 (13)	0.0423 (11)	0.0032 (9)	−0.0050 (9)	−0.0101 (10)
C3	0.0365 (13)	0.0347 (13)	0.0332 (10)	0.0021 (10)	−0.0129 (9)	−0.0059 (9)
C4	0.0382 (13)	0.0369 (13)	0.0226 (9)	−0.0042 (10)	−0.0041 (9)	−0.0032 (9)
C5	0.0257 (11)	0.0323 (12)	0.0265 (9)	−0.0009 (9)	−0.0011 (8)	−0.0033 (8)
C6	0.0245 (10)	0.0211 (10)	0.0260 (9)	0.0004 (8)	−0.0004 (8)	−0.0057 (8)
C7	0.0247 (11)	0.0224 (10)	0.0255 (9)	−0.0019 (8)	0.0021 (8)	−0.0001 (8)
C8	0.0296 (11)	0.0277 (11)	0.0274 (9)	0.0031 (10)	0.0052 (8)	−0.0017 (8)
C9	0.0265 (12)	0.0291 (11)	0.0336 (9)	0.0065 (9)	0.0043 (9)	0.0014 (9)
C10	0.0226 (11)	0.0268 (11)	0.0302 (9)	0.0014 (8)	0.0004 (8)	0.0042 (8)
C11	0.0246 (10)	0.0218 (10)	0.0232 (9)	−0.0019 (8)	0.0031 (7)	0.0013 (8)
C12	0.0204 (10)	0.0231 (10)	0.0259 (9)	0.0004 (8)	0.0005 (7)	0.0000 (8)
C13	0.0233 (11)	0.0255 (11)	0.0268 (9)	−0.0021 (8)	−0.0037 (8)	0.0032 (8)
C14	0.0208 (10)	0.0281 (10)	0.0206 (8)	−0.0015 (8)	−0.0006 (7)	0.0010 (7)
C15	0.0265 (11)	0.0205 (10)	0.0202 (8)	−0.0014 (8)	−0.0026 (7)	0.0035 (7)
C16	0.0244 (10)	0.0220 (10)	0.0245 (8)	−0.0004 (8)	−0.0009 (8)	0.0014 (8)
C17	0.0292 (11)	0.0268 (11)	0.0286 (9)	−0.0015 (9)	−0.0072 (8)	−0.0027 (8)
C18	0.0388 (12)	0.0278 (11)	0.0218 (8)	0.0020 (9)	−0.0041 (8)	−0.0015 (8)
C19	0.0303 (11)	0.0313 (12)	0.0253 (8)	0.0021 (9)	0.0029 (8)	0.0000 (9)
C20	0.0234 (11)	0.0319 (12)	0.0263 (8)	−0.0008 (9)	−0.0012 (8)	0.0032 (8)

O1—C13	1.242 (3)	C8—H8	0.9300
O2—C10	1.363 (2)	C9—C10	1.390 (3)
O2—H2	0.8200	C9—H9	0.9300
N1—C13	1.363 (2)	C10—C11	1.402 (3)
N1—C11	1.433 (2)	C11—C12	1.393 (3)
N1—C14	1.474 (3)	C12—H12	0.9300
C1—C2	1.386 (3)	C13—C16	1.466 (3)
C1—C6	1.396 (3)	C14—C15	1.507 (2)
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.384 (3)	C14—H14B	0.9700
C2—H2A	0.9300	C15—C20	1.380 (3)
C3—C4	1.381 (3)	C15—C16	1.382 (3)
C3—H3	0.9300	C16—C17	1.392 (3)
C4—C5	1.386 (3)	C17—C18	1.379 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.395 (3)	C18—C19	1.394 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.487 (3)	C19—C20	1.396 (3)
C7—C8	1.398 (3)	C19—H19	0.9300
C7—C12	1.398 (3)	C20—H20	0.9300
C8—C9	1.381 (3)
C10—O2—H2	109.5	C12—C11—C10	119.27 (17)
C13—N1—C11	127.30 (17)	C12—C11—N1	118.10 (17)
C13—N1—C14	112.13 (15)	C10—C11—N1	122.59 (16)
C11—N1—C14	120.56 (15)	C11—C12—C7	122.03 (18)
C2—C1—C6	121.00 (19)	C11—C12—H12	119.0
C2—C1—H1	119.5	C7—C12—H12	119.0
C6—C1—H1	119.5	O1—C13—N1	126.02 (18)
C3—C2—C1	120.3 (2)	O1—C13—C16	126.79 (18)
C3—C2—H2A	119.8	N1—C13—C16	107.19 (17)
C1—C2—H2A	119.8	N1—C14—C15	102.41 (15)
C4—C3—C2	119.3 (2)	N1—C14—H14A	111.3
C4—C3—H3	120.4	C15—C14—H14A	111.3
C2—C3—H3	120.4	N1—C14—H14B	111.3
C3—C4—C5	120.6 (2)	C15—C14—H14B	111.3
C3—C4—H4	119.7	H14A—C14—H14B	109.2
C5—C4—H4	119.7	C20—C15—C16	120.77 (16)
C4—C5—C6	120.8 (2)	C20—C15—C14	130.21 (18)
C4—C5—H5	119.6	C16—C15—C14	108.99 (16)
C6—C5—H5	119.6	C15—C16—C17	121.75 (18)
C5—C6—C1	117.99 (18)	C15—C16—C13	109.17 (15)
C5—C6—C7	120.34 (18)	C17—C16—C13	129.07 (19)
C1—C6—C7	121.66 (18)	C18—C17—C16	117.72 (19)
C8—C7—C12	117.76 (17)	C18—C17—H17	121.1
C8—C7—C6	121.68 (16)	C16—C17—H17	121.1
C12—C7—C6	120.54 (18)	C17—C18—C19	120.76 (17)
C9—C8—C7	120.55 (17)	C17—C18—H18	119.6
C9—C8—H8	119.7	C19—C18—H18	119.6
C7—C8—H8	119.7	C18—C19—C20	121.11 (19)
C8—C9—C10	121.62 (19)	C18—C19—H19	119.4
C8—C9—H9	119.2	C20—C19—H19	119.4
C10—C9—H9	119.2	C15—C20—C19	117.84 (19)
O2—C10—C9	117.24 (18)	C15—C20—H20	121.1
O2—C10—C11	123.97 (17)	C19—C20—H20	121.1
C9—C10—C11	118.74 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.79	2.575 (2)	162
C20—H20···O1i	0.93	2.37	3.283 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.79	2.575 (2)	162
C20—H20⋯O1i	0.93	2.37	3.283 (3)	168

Symmetry code: (i) .