2-Benzyl-3-hy-droxy-3-methyl-2,3-dihydro-1H-isoindol-1-one.

In the title compound, C(16)H(15)NO(2), the isoindoline ring system is approximately planar (mean deviation = 0.0186 Å) and makes a dihedral angle of 61.91 (4)° with the phenyl ring. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds.

Related literature

For background to the synthesis of the title compound, see: Griffiths et al. (1983 ▶); For its applications in synthesis, see: Winn & Zaugg (1968 ▶); Katsuhiko et al. (2006 ▶). For related structures, see: Wang et al. (2008 ▶); Orzeszko et al. (1998 ▶); Liu et al. (2009 ▶); Rosamilia et al. (2002 ▶).

Experimental

Crystal data

C16H15NO2

M = 253.29

Monoclinic,

a = 11.093 (4) Å

b = 11.604 (4) Å

c = 21.226 (7) Å

β = 101.777 (5)°

V = 2674.7 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.47 × 0.34 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

11602 measured reflections

3479 independent reflections

2673 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.11

3479 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021575/nr2026sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021575/nr2026Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021575/nr2026Isup3.cml

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

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

C16H15NO2	F(000) = 1072
Mr = 253.29	Dx = 1.258 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.093 (4) Å	Cell parameters from 4918 reflections
b = 11.604 (4) Å	θ = 2.6–29.1°
c = 21.226 (7) Å	µ = 0.08 mm−1
β = 101.777 (5)°	T = 153 K
V = 2674.7 (15) Å3	Block, colorless
Z = 8	0.47 × 0.34 × 0.23 mm

Rigaku AFC10/Saturn724+ diffractometer	2673 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.032
Graphite monochromator	θmax = 29.1°, θmin = 2.6°
Detector resolution: 28.5714 pixels mm-1	h = −12→15
phi and ω scans	k = −15→15
11602 measured reflections	l = −28→28
3479 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.056P)2 + 0.0264P] where P = (Fo2 + 2Fc2)/3
3479 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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	0.48310 (7)	0.73617 (7)	0.04556 (4)	0.0310 (2)
O2	0.49294 (7)	0.35635 (7)	0.07278 (4)	0.0321 (2)
N1	0.46720 (9)	0.54981 (8)	0.09038 (4)	0.0256 (2)
C1	0.53806 (10)	0.65930 (9)	0.09452 (5)	0.0263 (2)
C2	0.66237 (10)	0.61485 (9)	0.08633 (5)	0.0242 (2)
C3	0.76900 (10)	0.67523 (10)	0.08427 (5)	0.0300 (3)
H3	0.7719	0.7568	0.0880	0.036*
C4	0.87197 (11)	0.61253 (10)	0.07655 (6)	0.0314 (3)
H4	0.9459	0.6525	0.0746	0.038*
C5	0.86960 (11)	0.49285 (10)	0.07166 (5)	0.0290 (3)
H5	0.9418	0.4523	0.0672	0.035*
C6	0.76204 (10)	0.43254 (9)	0.07334 (5)	0.0257 (3)
H6	0.7589	0.3509	0.0699	0.031*
C7	0.65951 (10)	0.49583 (9)	0.08021 (5)	0.0227 (2)
C8	0.53351 (11)	0.45578 (9)	0.08088 (5)	0.0247 (2)
C9	0.33419 (10)	0.54720 (10)	0.08518 (5)	0.0295 (3)
H9A	0.3006	0.4809	0.0578	0.035*
H9B	0.2989	0.6181	0.0628	0.035*
C10	0.29071 (10)	0.53813 (10)	0.14795 (5)	0.0283 (3)
C11	0.33512 (12)	0.45438 (11)	0.19347 (6)	0.0352 (3)
H11	0.4002	0.4052	0.1873	0.042*
C12	0.28499 (13)	0.44209 (12)	0.24794 (6)	0.0409 (3)
H12	0.3159	0.3844	0.2788	0.049*
C13	0.19061 (13)	0.51312 (13)	0.25754 (6)	0.0433 (3)
H13	0.1557	0.5037	0.2945	0.052*
C14	0.14733 (12)	0.59773 (14)	0.21325 (7)	0.0470 (4)
H14	0.0832	0.6475	0.2200	0.056*
C15	0.19722 (11)	0.61047 (12)	0.15877 (6)	0.0391 (3)
H15	0.1671	0.6693	0.1285	0.047*
C16	0.54084 (11)	0.71985 (10)	0.15828 (6)	0.0339 (3)
H16A	0.5928	0.7887	0.1609	0.041*
H16B	0.5745	0.6675	0.1938	0.041*
H16C	0.4570	0.7423	0.1613	0.041*
H1O	0.4958 (12)	0.7058 (13)	0.0054 (7)	0.059 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (5)	0.0236 (4)	0.0314 (4)	0.0059 (3)	0.0092 (4)	0.0017 (3)
O2	0.0404 (5)	0.0228 (4)	0.0347 (5)	−0.0094 (3)	0.0114 (4)	−0.0022 (3)
N1	0.0259 (5)	0.0244 (5)	0.0278 (5)	−0.0027 (4)	0.0085 (4)	−0.0011 (4)
C1	0.0305 (6)	0.0207 (5)	0.0280 (6)	−0.0010 (4)	0.0069 (5)	−0.0011 (4)
C2	0.0286 (6)	0.0202 (5)	0.0240 (5)	−0.0011 (4)	0.0060 (4)	−0.0005 (4)
C3	0.0333 (6)	0.0208 (5)	0.0357 (6)	−0.0046 (5)	0.0063 (5)	−0.0001 (5)
C4	0.0281 (6)	0.0308 (6)	0.0355 (6)	−0.0052 (5)	0.0067 (5)	0.0040 (5)
C5	0.0290 (6)	0.0295 (6)	0.0290 (6)	0.0023 (5)	0.0073 (5)	0.0025 (5)
C6	0.0331 (7)	0.0202 (5)	0.0242 (5)	0.0007 (4)	0.0068 (5)	0.0009 (4)
C7	0.0287 (6)	0.0193 (5)	0.0202 (5)	−0.0024 (4)	0.0054 (4)	0.0007 (4)
C8	0.0322 (6)	0.0225 (5)	0.0201 (5)	−0.0037 (4)	0.0071 (4)	0.0001 (4)
C9	0.0266 (6)	0.0361 (6)	0.0260 (6)	−0.0022 (5)	0.0059 (5)	0.0008 (5)
C10	0.0238 (6)	0.0353 (6)	0.0256 (6)	−0.0062 (5)	0.0050 (4)	−0.0023 (5)
C11	0.0401 (7)	0.0376 (7)	0.0284 (6)	0.0017 (5)	0.0080 (5)	−0.0007 (5)
C12	0.0494 (9)	0.0469 (8)	0.0259 (6)	−0.0046 (6)	0.0069 (6)	0.0030 (5)
C13	0.0405 (8)	0.0640 (9)	0.0279 (6)	−0.0108 (7)	0.0132 (5)	−0.0030 (6)
C14	0.0350 (7)	0.0681 (10)	0.0419 (8)	0.0064 (7)	0.0174 (6)	0.0024 (7)
C15	0.0292 (7)	0.0531 (8)	0.0367 (7)	0.0031 (6)	0.0107 (5)	0.0069 (6)
C16	0.0387 (7)	0.0311 (6)	0.0325 (6)	0.0011 (5)	0.0086 (5)	−0.0084 (5)

O1—C1	1.4102 (13)	C7—C8	1.4757 (16)
O1—H1O	0.960 (15)	C9—C10	1.5103 (16)
O2—C8	1.2377 (13)	C9—H9A	0.9900
N1—C8	1.3538 (14)	C9—H9B	0.9900
N1—C9	1.4573 (16)	C10—C11	1.3880 (17)
N1—C1	1.4871 (14)	C10—C15	1.3894 (17)
C1—C2	1.5151 (16)	C11—C12	1.3888 (18)
C1—C16	1.5196 (15)	C11—H11	0.9500
C2—C3	1.3831 (15)	C12—C13	1.380 (2)
C2—C7	1.3870 (15)	C12—H12	0.9500
C3—C4	1.3918 (16)	C13—C14	1.376 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3925 (17)	C14—C15	1.3879 (18)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.3900 (16)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.3864 (15)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C1—O1—H1O	107.6 (9)	N1—C9—C10	115.80 (10)
C8—N1—C9	122.99 (10)	N1—C9—H9A	108.3
C8—N1—C1	113.62 (9)	C10—C9—H9A	108.3
C9—N1—C1	122.48 (9)	N1—C9—H9B	108.3
O1—C1—N1	110.67 (9)	C10—C9—H9B	108.3
O1—C1—C2	113.42 (9)	H9A—C9—H9B	107.4
N1—C1—C2	100.65 (8)	C11—C10—C15	118.60 (11)
O1—C1—C16	106.91 (9)	C11—C10—C9	122.08 (11)
N1—C1—C16	111.22 (9)	C15—C10—C9	119.16 (11)
C2—C1—C16	113.96 (9)	C10—C11—C12	120.40 (12)
C3—C2—C7	120.32 (10)	C10—C11—H11	119.8
C3—C2—C1	129.45 (10)	C12—C11—H11	119.8
C7—C2—C1	110.23 (9)	C13—C12—C11	120.42 (13)
C2—C3—C4	117.82 (10)	C13—C12—H12	119.8
C2—C3—H3	121.1	C11—C12—H12	119.8
C4—C3—H3	121.1	C14—C13—C12	119.65 (13)
C3—C4—C5	121.78 (10)	C14—C13—H13	120.2
C3—C4—H4	119.1	C12—C13—H13	120.2
C5—C4—H4	119.1	C13—C14—C15	120.15 (13)
C6—C5—C4	120.23 (11)	C13—C14—H14	119.9
C6—C5—H5	119.9	C15—C14—H14	119.9
C4—C5—H5	119.9	C14—C15—C10	120.77 (13)
C7—C6—C5	117.57 (10)	C14—C15—H15	119.6
C7—C6—H6	121.2	C10—C15—H15	119.6
C5—C6—H6	121.2	C1—C16—H16A	109.5
C6—C7—C2	122.26 (10)	C1—C16—H16B	109.5
C6—C7—C8	129.28 (10)	H16A—C16—H16B	109.5
C2—C7—C8	108.44 (9)	C1—C16—H16C	109.5
O2—C8—N1	125.37 (11)	H16A—C16—H16C	109.5
O2—C8—C7	127.62 (10)	H16B—C16—H16C	109.5
N1—C8—C7	106.98 (9)
C8—N1—C1—O1	119.71 (10)	C1—C2—C7—C8	2.63 (12)
C9—N1—C1—O1	−49.64 (13)	C9—N1—C8—O2	−7.00 (17)
C8—N1—C1—C2	−0.51 (11)	C1—N1—C8—O2	−176.29 (10)
C9—N1—C1—C2	−169.86 (9)	C9—N1—C8—C7	171.34 (9)
C8—N1—C1—C16	−121.59 (10)	C1—N1—C8—C7	2.05 (12)
C9—N1—C1—C16	69.06 (12)	C6—C7—C8—O2	−3.10 (19)
O1—C1—C2—C3	60.18 (15)	C2—C7—C8—O2	175.41 (11)
N1—C1—C2—C3	178.40 (11)	C6—C7—C8—N1	178.60 (10)
C16—C1—C2—C3	−62.48 (15)	C2—C7—C8—N1	−2.89 (12)
O1—C1—C2—C7	−119.60 (10)	C8—N1—C9—C10	99.09 (13)
N1—C1—C2—C7	−1.37 (11)	C1—N1—C9—C10	−92.55 (12)
C16—C1—C2—C7	117.75 (11)	N1—C9—C10—C11	−51.07 (15)
C7—C2—C3—C4	−0.60 (16)	N1—C9—C10—C15	133.51 (12)
C1—C2—C3—C4	179.64 (10)	C15—C10—C11—C12	1.30 (18)
C2—C3—C4—C5	−0.64 (17)	C9—C10—C11—C12	−174.15 (11)
C3—C4—C5—C6	1.07 (17)	C10—C11—C12—C13	−0.1 (2)
C4—C5—C6—C7	−0.23 (16)	C11—C12—C13—C14	−1.0 (2)
C5—C6—C7—C2	−1.03 (16)	C12—C13—C14—C15	0.9 (2)
C5—C6—C7—C8	177.31 (10)	C13—C14—C15—C10	0.3 (2)
C3—C2—C7—C6	1.47 (16)	C11—C10—C15—C14	−1.39 (19)
C1—C2—C7—C6	−178.73 (9)	C9—C10—C15—C14	174.19 (12)
C3—C2—C7—C8	−177.17 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.960 (15)	1.836 (15)	2.7938 (14)	175.3 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2i	0.960 (15)	1.836 (15)	2.7938 (14)	175.3 (12)

Symmetry code: (i) .