2-{[(E)-2-Hy-droxy-benzyl-idene]amino}-1H-isoindole-1,3(2H)-dione.

In the title compound, C(15)H(10)N(2)O(3), the isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds are observed.

Related literature

Based on the multiple binding sites of acetyl­cholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al. (2009 ▶). n class="Chemical">Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al. (2009 ▶). For the biological activity of Schiff bases, see: Singh et al. (2006 ▶); Sithambaram et al. (2006 ▶); Walsh et al. (1996 ▶). For a related structure, see: Jing et al. (2007 ▶).

Experimental

Crystal data

C15H10N2O3

M = 266.25

Monoclinic,

a = 7.0877 (2) Å

b = 8.2400 (4) Å

c = 21.2752 (7) Å

β = 92.659 (3)°

V = 1241.19 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD n class="Chemical">area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.982, T max = 0.988

11806 measured reflections

2184 independent reflections

1541 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.10

2184 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); moleculn class="Chemical">ar graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038407/wn2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038407/wn2411Isup2.hkl

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

C15H10N2O3	F(000) = 552
Mr = 266.25	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Melting point: 465 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0877 (2) Å	Cell parameters from 2184 reflections
b = 8.2400 (4) Å	θ = 2.7–25.0°
c = 21.2752 (7) Å	µ = 0.10 mm−1
β = 92.659 (3)°	T = 293 K
V = 1241.19 (8) Å3	Plate, yellow
Z = 4	0.22 × 0.15 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1541 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.982, Tmax = 0.988	k = −9→9
11806 measured reflections	l = −25→25

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.0801P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2184 reflections	Δρmax = 0.10 e Å−3
182 parameters	Δρmin = −0.11 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: 0.0088 (16)

Experimental. IR ν(Nujolmull, cm-1): 1768 and 1725 (C=O), 1617 (HC=N), 3386 (Ph—OH). 1H NMR (DMSO-d6, p.p.m.): 10.67 (s, 1H, Ph—OH), 9.45 (s, 1H, HC=N), 6.92–7.91 (m, 4H, Ar—H). FAB-MS: m/z = 267 [M+1]+, Anal. Calc. for C15H10N2O3; C, 67.67; H, 3.79; N, 10.52; O, 18.03; Found: C, 67.05; H, 3.81; N, 10.68; O, 17.98,; Electronic spectra: 289 nm and 334 nm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O3	−0.27271 (15)	0.27296 (16)	0.07498 (5)	0.0836 (4)
O4	0.28488 (17)	0.31121 (18)	−0.02433 (5)	0.0877 (4)
O5	0.00226 (15)	0.52524 (17)	0.19986 (5)	0.0846 (4)
H5	−0.0194	0.4752	0.1670	0.127*
N1	0.02621 (17)	0.31346 (16)	0.03847 (5)	0.0579 (4)
N2	0.08319 (18)	0.40089 (16)	0.09127 (5)	0.0591 (4)
C1	−0.3130 (3)	0.0248 (2)	−0.11364 (9)	0.0780 (5)
H1	−0.4146	−0.0282	−0.1338	0.094*
C2	−0.1434 (3)	0.0318 (2)	−0.14198 (8)	0.0798 (5)
H2	−0.1320	−0.0162	−0.1812	0.096*
C3	0.0112 (3)	0.1090 (2)	−0.11336 (8)	0.0739 (5)
H3	0.1262	0.1138	−0.1327	0.089*
C4	−0.0109 (2)	0.1786 (2)	−0.05531 (7)	0.0580 (4)
C5	−0.1815 (2)	0.1703 (2)	−0.02662 (7)	0.0578 (4)
C6	−0.3351 (2)	0.0955 (2)	−0.05535 (8)	0.0716 (5)
H6	−0.4506	0.0923	−0.0363	0.086*
C7	0.1244 (2)	0.2722 (2)	−0.01510 (7)	0.0614 (4)
C8	−0.1610 (2)	0.2551 (2)	0.03459 (7)	0.0607 (4)
C9	0.2541 (2)	0.4496 (2)	0.09978 (7)	0.0610 (4)
H9	0.3422	0.4266	0.0700	0.073*
C10	0.3099 (2)	0.54030 (19)	0.15573 (7)	0.0557 (4)
C11	0.4953 (2)	0.5961 (2)	0.16350 (8)	0.0700 (5)
H11	0.5798	0.5748	0.1324	0.084*
C12	0.5558 (3)	0.6816 (2)	0.21590 (9)	0.0783 (5)
H12	0.6801	0.7176	0.2204	0.094*
C13	0.4304 (3)	0.7134 (2)	0.26175 (9)	0.0781 (5)
H13	0.4705	0.7720	0.2973	0.094*
C14	0.2476 (3)	0.6602 (2)	0.25587 (8)	0.0741 (5)
H14	0.1648	0.6823	0.2874	0.089*
C15	0.1854 (2)	0.5737 (2)	0.20321 (8)	0.0610 (4)

	U11	U22	U33	U12	U13	U23
O3	0.0731 (8)	0.1092 (11)	0.0704 (7)	−0.0031 (7)	0.0216 (6)	−0.0101 (7)
O4	0.0713 (8)	0.1189 (12)	0.0746 (8)	−0.0043 (7)	0.0206 (6)	−0.0070 (7)
O5	0.0675 (8)	0.1089 (11)	0.0789 (8)	−0.0129 (7)	0.0191 (6)	−0.0184 (7)
N1	0.0613 (8)	0.0631 (9)	0.0498 (7)	0.0052 (6)	0.0078 (6)	0.0018 (7)
N2	0.0640 (9)	0.0584 (9)	0.0550 (8)	0.0062 (7)	0.0045 (6)	0.0027 (6)
C1	0.0967 (14)	0.0658 (13)	0.0705 (11)	0.0020 (10)	−0.0077 (10)	−0.0015 (10)
C2	0.1067 (15)	0.0726 (14)	0.0597 (10)	0.0146 (11)	0.0006 (10)	−0.0049 (9)
C3	0.0871 (12)	0.0750 (13)	0.0606 (10)	0.0132 (10)	0.0139 (9)	0.0029 (9)
C4	0.0706 (10)	0.0528 (10)	0.0510 (8)	0.0114 (8)	0.0071 (7)	0.0108 (8)
C5	0.0692 (10)	0.0525 (10)	0.0520 (8)	0.0090 (8)	0.0047 (7)	0.0111 (7)
C6	0.0745 (11)	0.0693 (12)	0.0711 (11)	0.0009 (9)	0.0043 (9)	0.0073 (10)
C7	0.0654 (10)	0.0640 (12)	0.0558 (9)	0.0106 (9)	0.0127 (8)	0.0093 (8)
C8	0.0641 (10)	0.0632 (12)	0.0556 (9)	0.0072 (8)	0.0105 (8)	0.0083 (8)
C9	0.0626 (10)	0.0622 (11)	0.0589 (9)	0.0106 (8)	0.0100 (7)	0.0092 (8)
C10	0.0587 (9)	0.0502 (10)	0.0581 (9)	0.0058 (7)	0.0031 (7)	0.0097 (7)
C11	0.0626 (11)	0.0696 (13)	0.0781 (11)	0.0025 (9)	0.0079 (8)	0.0107 (10)
C12	0.0713 (11)	0.0699 (13)	0.0928 (14)	−0.0089 (9)	−0.0062 (10)	0.0072 (11)
C13	0.0924 (14)	0.0607 (13)	0.0797 (12)	−0.0031 (10)	−0.0130 (10)	−0.0018 (10)
C14	0.0827 (12)	0.0714 (13)	0.0687 (11)	0.0012 (10)	0.0076 (9)	−0.0059 (10)
C15	0.0612 (10)	0.0568 (11)	0.0653 (10)	0.0005 (8)	0.0048 (8)	0.0043 (8)

O3—C8	1.2041 (17)	C4—C7	1.473 (2)
O4—C7	1.2068 (17)	C5—C6	1.370 (2)
O5—C15	1.3568 (18)	C5—C8	1.479 (2)
O5—H5	0.8200	C6—H6	0.9300
N1—N2	1.3791 (17)	C9—C10	1.445 (2)
N1—C7	1.4044 (19)	C9—H9	0.9300
N1—C8	1.4105 (19)	C10—C11	1.395 (2)
N2—C9	1.2811 (18)	C10—C15	1.399 (2)
C1—C2	1.371 (2)	C11—C12	1.371 (2)
C1—C6	1.386 (2)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.375 (2)
C2—C3	1.384 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.368 (2)
C3—C4	1.377 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.383 (2)
C4—C5	1.381 (2)	C14—H14	0.9300
C15—O5—H5	109.5	N1—C7—C4	105.31 (13)
N2—N1—C7	130.54 (13)	O3—C8—N1	124.36 (15)
N2—N1—C8	117.71 (11)	O3—C8—C5	130.20 (15)
C7—N1—C8	111.74 (13)	N1—C8—C5	105.43 (12)
C9—N2—N1	121.21 (13)	N2—C9—C10	119.96 (14)
C2—C1—C6	120.94 (17)	N2—C9—H9	120.0
C2—C1—H1	119.5	C10—C9—H9	120.0
C6—C1—H1	119.5	C11—C10—C15	118.16 (15)
C1—C2—C3	121.24 (17)	C11—C10—C9	119.24 (15)
C1—C2—H2	119.4	C15—C10—C9	122.60 (14)
C3—C2—H2	119.4	C12—C11—C10	121.56 (16)
C4—C3—C2	117.71 (16)	C12—C11—H11	119.2
C4—C3—H3	121.1	C10—C11—H11	119.2
C2—C3—H3	121.1	C11—C12—C13	119.14 (17)
C3—C4—C5	120.97 (16)	C11—C12—H12	120.4
C3—C4—C7	129.82 (15)	C13—C12—H12	120.4
C5—C4—C7	109.20 (13)	C14—C13—C12	120.96 (18)
C6—C5—C4	121.26 (15)	C14—C13—H13	119.5
C6—C5—C8	130.43 (14)	C12—C13—H13	119.5
C4—C5—C8	108.30 (14)	C13—C14—C15	120.29 (17)
C5—C6—C1	117.88 (16)	C13—C14—H14	119.9
C5—C6—H6	121.1	C15—C14—H14	119.9
C1—C6—H6	121.1	O5—C15—C14	117.54 (14)
O4—C7—N1	125.03 (16)	O5—C15—C10	122.57 (15)
O4—C7—C4	129.65 (15)	C14—C15—C10	119.88 (15)
C7—N1—N2—C9	−5.3 (2)	C7—N1—C8—O3	178.98 (14)
C8—N1—N2—C9	175.89 (14)	N2—N1—C8—C5	178.99 (12)
C6—C1—C2—C3	0.2 (3)	C7—N1—C8—C5	−0.04 (17)
C1—C2—C3—C4	0.1 (3)	C6—C5—C8—O3	3.4 (3)
C2—C3—C4—C5	0.4 (2)	C4—C5—C8—O3	−177.93 (16)
C2—C3—C4—C7	−177.72 (16)	C6—C5—C8—N1	−177.66 (16)
C3—C4—C5—C6	−1.3 (2)	C4—C5—C8—N1	1.02 (17)
C7—C4—C5—C6	177.25 (15)	N1—N2—C9—C10	−179.69 (13)
C3—C4—C5—C8	179.92 (15)	N2—C9—C10—C11	−178.34 (14)
C7—C4—C5—C8	−1.58 (17)	N2—C9—C10—C15	2.3 (2)
C4—C5—C6—C1	1.5 (2)	C15—C10—C11—C12	−0.1 (2)
C8—C5—C6—C1	−179.97 (16)	C9—C10—C11—C12	−179.50 (15)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C12—C13	−0.2 (3)
N2—N1—C7—O4	−1.0 (3)	C11—C12—C13—C14	0.4 (3)
C8—N1—C7—O4	177.88 (15)	C12—C13—C14—C15	−0.3 (3)
N2—N1—C7—C4	−179.74 (14)	C13—C14—C15—O5	−179.50 (15)
C8—N1—C7—C4	−0.87 (17)	C13—C14—C15—C10	0.0 (3)
C3—C4—C7—O4	1.2 (3)	C11—C10—C15—O5	179.69 (14)
C5—C4—C7—O4	−177.15 (17)	C9—C10—C15—O5	−0.9 (2)
C3—C4—C7—N1	179.85 (16)	C11—C10—C15—C14	0.2 (2)
C5—C4—C7—N1	1.52 (17)	C9—C10—C15—C14	179.56 (15)
N2—N1—C8—O3	−2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.90	2.6152 (16)	145
C9—H9···O4	0.93	2.24	2.8937 (19)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	1.90	2.6152 (16)	145
C9—H9⋯O4	0.93	2.24	2.8937 (19)	127