3-Hydr-oxy-3-phenyl-isoindolin-1-one 0.33-hydrate.

Abstract

The asymmetric unit of the title compound, C(14)H(11)NO(2)·0.33H(2)O, contains three 3-hydr-oxy-3-phenyl-isoindolin-1-one (HPIO) mol-ecules and one water mol-ecule. The three independent HPIO mol-ecules differ in the orientations of hydr-oxy and phenyl groups substituted at the 3-position with respect to the planar [r.m.s. deviations of 0.0173, 0.0170 and 0.0102 Å] dihydro-isoindolin-1-one ring system. In the crystal structure, mol-ecules are linked into a three-dimensional network by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds.

Full text

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3-Hydroxy-3-phenylisoindolin-1-one
0.33-hydrate
Shan Liu,aXiao-Li Zhang,aWen-Hong Zhangband
Hong-Jun Zhuc*
aDepartment of Chemical Engineering, Nanjing College of Chemical Technology,
Nanjing 210048, People’s Republic of China,bInstitute of Plant Protection, Jiangsu
Academy of Agricultural Sciences, Nanjing 210014, People’s Republic of China, and
cDepartment of Applied Chemistry, College of Science, Nanjing University of
Technology, Nanjing 210009, People’s Republic of China
Correspondence e-mail: zhuhjnjut@hotmail.com
Received 23 October 2009; accepted 2 November 2009
Key indicators: single-crystal X-ray study; T = 298 K; mean ?(C–C) = 0.005 A ˚;
R factor = 0.057; wR factor = 0.181; data-to-parameter ratio = 14.6.
The asymmetric unit of the title compound, C14H11NO2?-
0.33H2O, contains three 3-hydroxy-3-phenylisoindolin-1-one
(HPIO) molecules and one water molecule. The three
independent HPIO molecules differ in the orientations of
hydroxy and phenyl groups substituted at the 3-position with
respect to the planar [r.m.s. deviations of 0.0173, 0.0170 and
0.0102 A˚] dihydroisoindolin-1-one ring system. In the crystal
structure, molecules are linked into a three-dimensional
network by O—H???O, N—H???O and C—H???O hydrogen
bonds.
Related literature
For general background, see: Antoniadis et al. (1994); Tonzola
et al. (2003). For bond-length data, see: Allen et al. (1987). For
the preparation, see: Imai et al. (1975).
Experimental
Crystal data
C14H11NO2?0.33H2O
Mr= 231.24
Triclinic, P1
a = 11.709 (2) A˚
b = 12.621 (3) A˚
c = 14.572 (3) A˚
? = 67.84 (3)?
? = 74.65 (3)?
? = 64.54 (3)?
V = 1787.1 (8) A˚3
Z = 6
Mo K? radiation
? = 0.09 mm?1
T = 298 K
0.30 ? 0.20 ? 0.20 mm
Data collection
Enraf–Nonius CAD-4
diffractometer
Absorption correction: scan
(North et al., 1968)
Tmin= 0.944, Tmax= 0.963
6996 measured reflections
6996 independent reflections
4605 reflections with I > 2?(I)
3 standard reflections
every 200 reflections
intensity decay: none
Refinement
R[F2> 2?(F2)] = 0.057
wR(F2) = 0.181
S = 1.12
6996 reflections
478 parameters
H atoms treated by a mixture of
independent and constrained
refinement
??max= 0.24 e A˚?3
??min= ?0.25 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
O1W—H1WA???O2i
O1W—H1WB???O4i
O1—H1A???O3i
O3—H3B???O6i
O5—H5B???O1W
N1—H1B???O6
N2—H2B???O5
N3—H3C???O4
C24—H24???O2ii
C34—H34???O2iii
Symmetry
?x þ 1;?y þ 1;?z þ 1.
D—HH???AD???AD—H???A
0.92 (6)
0.86 (6)
0.82
0.82
0.82
0.86
0.86
0.86
0.93
0.93
1.78 (6)
2.01 (6)
1.96
1.83
1.85
2.21
2.16
2.04
2.44
2.58
2.697 (4)
2.871 (4)
2.777 (3)
2.634 (3)
2.668 (5)
2.981 (3)
3.003 (3)
2.873 (3)
3.284 (4)
3.387 (6)
175 (6)
177 (7)
179
166
174
149
167
162
151
146
codes: (i)
?x;?y þ 1;?z þ 1; (ii)
?x;?y þ 2;?z þ 1; (iii)
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
refinement: CAD-4 Software; data reduction: XCAD4 (Harms &
Wocadlo, 1995); 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: SHELXTL.
The authors thank the Center of Testing and Analysis,
Nanjing University, for support.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: CI2953).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Antoniadis, H., Hsieh, B. R., Abkowitz, M. A., Jenekhe, S. A. & Stolka, M.
(1994). Synth. Met. 62, 265–271.
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Nether-
lands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Imai, Y., Johnson, E. F., Katto, T., Kurihara, M. & Stille, J. K. (1975). J. Polym.
Sci. Part A Polym. Chem. 13, 2233–2249.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–
359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tonzola, C. J., Alam, M. M., Kaminsky, W. & Jenekhe, S. A. (2003). J. Am.
Chem. Soc. 125, 13548–13558.
organic compounds
Acta Cryst. (2009). E65, o3011doi:10.1107/S160053680904608X Liu et al.
o3011
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2009). E65, o3011 [ doi:10.1107/S160053680904608X ]
3-Hydroxy-3-phenylisoindolin-1-one 0.33-hydrate
S. Liu, X.-L. Zhang, W.-H. Zhang and H.-J. Zhu
Comment
HPIO is an important intermediate used to synthesize the monomer 2-benzoylbenzenamine, which can be utilized to syn-
thesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for ap-
plications in electronic and optoelectronic devices including light-emitting diodes, thin film transistors, and photovoltaic
cells (Antoniadis et al., 1994). We report here the crystal structure of the title compound which is of interest to us in the field.
The asymmetric unit of the title compound contains three HPIO molecules and one water molecule (Fig. 1). Bond lengths
(Allen et al., 1987) and angles are within normal ranges. In all independent molecules, dihydroisoindolin-1-one ring systems
are planar. The five membered ring forms dihedral angles of 2.3 (2) and 81.2 (2) °, respectively, with the fused and substituted
benzene rings in molecule A (with N1) [0.6 (2) and 68.1 (2)° in molecule B (with N2) and 1.2 (2) and 75.5 (2)°, respectively,
in molecule C (with N3)].
In the crystal structure, molecules are linked via intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds
(Table 1 and Fig. 2) forming a three-dimensional network.
Experimental
3-Hydroxy-3-phenylisoindolin-1-one (HPIO) was prepared by the method reported in the literature (Imai et al., 1975). Single
crystals of the title compound were obtained by dissolving HPIO (0.5 g, 2.22 mmol) in methanol (50 ml) and evaporating
the solvent slowly at room temperature for about 10 d.
Refinement
Water H atoms were located in a difference map and their positional parameters were refined, with Uiso(H) = 1.5Ueq(O).
The remaining H atoms were positioned geometrically [O-H = 0.82 Å, N-H = 0.86 Å and C-H = 0.93 Å] and constrained to
ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H and x = 1.5 for other H.
Figures
Fig. 1. The asymmetric unit of the title compound, with the atom-numbering scheme. Dis-
placement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as
dashed lines.

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Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
3-Hydroxy-3-phenylisoindolin-1-one 0.33-hydrate
Crystal data
C14H11NO2·0.33H2O
Mr = 231.24
Z = 6
F000 = 728
Dx = 1.289 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 25 reflections
θ = 10–13º
µ = 0.09 mm−1
T = 298 K
Block, colourless
0.30 × 0.20 × 0.20 mm
Triclinic, P1
Hall symbol: -P 1
a = 11.709 (2) Å
b = 12.621 (3) Å
c = 14.572 (3) Å
α = 67.84 (3)º
β = 74.65 (3)º
γ = 64.54 (3)º
V = 1787.1 (8) Å3
Data collection
Enraf–Nonius CAD-4
diffractometer
Radiation source: fine-focus sealed tube
Monochromator: graphite
T = 298 K
ω/2θ scans
Absorption correction: ψ scan
(North et al., 1968)
Tmin = 0.944, Tmax = 0.963
6996 measured reflections
6996 independent reflections
4605 reflections with I > 2σ(I)
Rint = 0.0000
θmax = 26.0º
θmin = 1.5º
h = −13→14
k = −14→15
l = 0→17
3 standard reflections
every 200 reflections
intensity decay: none
Refinement
Refinement on F2
Secondary atom site location: difference Fourier map
Least-squares matrix: full
Hydrogen site location: inferred from neighbouring
sites
H atoms treated by a mixture of
independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0652P)2 + 1.1495P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
R[F2 > 2σ(F2)] = 0.057
wR(F2) = 0.181
S = 1.12

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6996 reflections
Δρmax = 0.24 e Å−3
Δρmin = −0.25 e Å−3
478 parameters
Primary atom site location: structure-invariant direct
methods
Extinction correction: none
Special details
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 mat-
rix. 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, convention-
al 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)
x
0.1027 (2)
0.0724
0.0699 (2)
0.1280 (2)
0.1048
0.5483 (4)
0.6273
0.5120 (4)
0.5661
0.3948 (3)
0.3708
0.3124 (3)
0.3507 (4)
0.2975
0.4669 (5)
0.4907
0.1856 (3)
0.1136 (2)
0.1633 (3)
0.1674 (3)
0.1393
0.2148 (3)
0.2205
0.2535 (3)
0.2828
0.2502 (3)
0.2779
0.2041 (3)
y
0.2239 (2)
0.2167
0.61190 (19)
0.4033 (2)
0.4063
0.0646 (4)
0.0152
0.1896 (4)
0.2266
0.2610 (3)
0.3462
0.2090 (3)
0.0836 (3)
0.0453
0.0142 (4)
−0.0708
0.2888 (2)
0.5052 (3)
0.4612 (3)
0.5279 (3)
0.6134
0.4633 (4)
0.5053
0.3369 (4)
0.2952
0.2704 (3)
0.1849
0.3352 (3)
z
0.95488 (15)
0.9139
0.79620 (16)
0.83025 (17)
0.7778
0.7840 (4)
0.7599
0.7529 (3)
0.7065
0.7906 (3)
0.7689
0.8598 (2)
0.8886 (4)
0.9346
0.8503 (5)
0.8709
0.9045 (2)
0.8493 (2)
0.9459 (2)
1.0002 (2)
0.9766
1.0911 (2)
1.1291
1.1254 (2)
1.1876
1.0709 (2)
1.0945
0.9794 (2)
Uiso*/Ueq
0.0503 (5)
0.075*
0.0542 (5)
0.0439 (6)
0.053*
0.0899 (13)
0.108*
0.0794 (12)
0.095*
0.0639 (9)
0.077*
0.0434 (7)
0.0882 (14)
0.106*
0.119 (2)
0.143*
0.0386 (6)
0.0399 (6)
0.0407 (6)
0.0539 (8)
0.065*
0.0603 (9)
0.072*
0.0591 (9)
0.071*
0.0510 (7)
0.061*
0.0390 (6)
O1
H1A
O2
N1
H1B
C1
H1
C2
H2
C3
H3
C4
C5
H5
C6
H6
C7
C8
C9
C10
H10
C11
H11
C12
H12
C13
H13
C14