2-(2-Hydroxy­ethyl)isoindoline-1,3-dione

In the title mol­ecule, C₁₀H₉N0₃, the phthalimide unit is essentially planar and the hydroxy­ethyl substituent adopts a coiled conformation, with an N—C—C—O torsion angle of −65.3 (3)°. In the crystal structure, inter­molecular O—H...O hydrogen bonds link mol­ecules into one-dimensional chains along the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.112
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

2-(2-hydroxyethyl)isoindoline-1,3-dione

Crystal data

C10H9NO3	F(000) = 400
Mr = 191.18	Dx = 1.423 Mg m^−3
Monoclinic, P21/n	Melting point = 401–403 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.090 (4) Å	Cell parameters from 822 reflections
b = 7.888 (3) Å	θ = 2.4–21.7°
c = 11.591 (4) Å	µ = 0.11 mm^−1
β = 104.734 (6)°	T = 294 K
V = 892.2 (6) Å^3	Block, colourless
Z = 4	0.30 × 0.24 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	1566 independent reflections
Radiation source: fine-focus sealed tube	962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→11
Tmin = 0.969, Tmax = 0.989	k = −5→9
3550 measured reflections	l = −13→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.0263P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
1566 reflections	Δρmax = 0.13 e Å^−3
129 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (5)

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.71596 (17)	−0.0229 (2)	0.78380 (15)	0.0603 (5)
O2	0.59922 (17)	0.2304 (2)	0.41841 (15)	0.0637 (5)
O3	0.92827 (19)	0.2970 (2)	0.57063 (17)	0.0716 (6)
H3	0.8828	0.3597	0.6020	0.107*
N1	0.69045 (17)	0.0944 (2)	0.59790 (15)	0.0415 (5)
C1	0.6521 (2)	0.0658 (3)	0.7025 (2)	0.0433 (6)
C2	0.5223 (2)	0.1591 (3)	0.6921 (2)	0.0412 (6)
C3	0.4404 (2)	0.1755 (3)	0.7698 (2)	0.0555 (7)
H3A	0.4635	0.1240	0.8444	0.067*
C4	0.3218 (3)	0.2719 (3)	0.7330 (3)	0.0647 (8)
H4	0.2632	0.2826	0.7829	0.078*
C5	0.2895 (3)	0.3520 (3)	0.6234 (3)	0.0655 (8)
H5	0.2105	0.4177	0.6015	0.079*
C6	0.3728 (2)	0.3363 (3)	0.5454 (2)	0.0548 (7)
H6	0.3510	0.3896	0.4714	0.066*
C7	0.4888 (2)	0.2388 (3)	0.58191 (19)	0.0394 (6)
C8	0.5941 (2)	0.1951 (3)	0.5187 (2)	0.0430 (6)
C9	0.8147 (2)	0.0269 (3)	0.5728 (2)	0.0506 (7)
H9A	0.8015	0.0187	0.4871	0.061*
H9B	0.8312	−0.0864	0.6058	0.061*
C10	0.9387 (2)	0.1363 (3)	0.6245 (2)	0.0593 (7)
H10A	0.9487	0.1499	0.7095	0.071*
H10B	1.0200	0.0797	0.6138	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0585 (11)	0.0666 (12)	0.0547 (12)	0.0013 (9)	0.0125 (9)	0.0186 (9)
O2	0.0702 (12)	0.0808 (13)	0.0472 (11)	0.0101 (10)	0.0279 (9)	0.0124 (9)
O3	0.0775 (15)	0.0673 (13)	0.0820 (14)	−0.0147 (10)	0.0421 (11)	−0.0115 (10)
N1	0.0416 (11)	0.0436 (12)	0.0436 (12)	0.0013 (9)	0.0185 (9)	−0.0001 (9)
C1	0.0471 (14)	0.0443 (14)	0.0401 (14)	−0.0091 (12)	0.0137 (11)	0.0003 (11)
C2	0.0414 (13)	0.0413 (13)	0.0450 (14)	−0.0085 (10)	0.0188 (11)	−0.0049 (10)
C3	0.0576 (17)	0.0616 (18)	0.0551 (16)	−0.0149 (14)	0.0289 (13)	−0.0052 (12)
C4	0.0557 (18)	0.0693 (19)	0.082 (2)	−0.0106 (15)	0.0409 (16)	−0.0204 (16)
C5	0.0469 (16)	0.0630 (19)	0.090 (2)	0.0043 (13)	0.0244 (16)	−0.0122 (16)
C6	0.0488 (16)	0.0558 (16)	0.0610 (17)	0.0042 (13)	0.0160 (13)	−0.0008 (12)
C7	0.0362 (13)	0.0379 (14)	0.0465 (14)	−0.0042 (10)	0.0147 (11)	−0.0074 (10)
C8	0.0459 (14)	0.0402 (14)	0.0451 (15)	−0.0040 (11)	0.0155 (12)	0.0017 (11)
C9	0.0510 (15)	0.0469 (15)	0.0596 (17)	0.0061 (12)	0.0248 (13)	−0.0035 (11)
C10	0.0476 (16)	0.0704 (19)	0.0653 (18)	0.0056 (14)	0.0240 (13)	−0.0072 (14)

Geometric parameters (Å, º)

O1—C1	1.218 (3)	C4—C5	1.382 (4)
O2—C8	1.209 (3)	C4—H4	0.9300
O3—C10	1.405 (3)	C5—C6	1.387 (3)
O3—H3	0.8200	C5—H5	0.9300
N1—C1	1.382 (3)	C6—C7	1.375 (3)
N1—C8	1.401 (3)	C6—H6	0.9300
N1—C9	1.458 (3)	C7—C8	1.477 (3)
C1—C2	1.480 (3)	C9—C10	1.512 (3)
C2—C3	1.376 (3)	C9—H9A	0.9700
C2—C7	1.386 (3)	C9—H9B	0.9700
C3—C4	1.390 (3)	C10—H10A	0.9700
C3—H3A	0.9300	C10—H10B	0.9700
C10—O3—H3	109.5	C7—C6—H6	121.3
C1—N1—C8	111.44 (18)	C5—C6—H6	121.3
C1—N1—C9	124.21 (19)	C6—C7—C2	121.8 (2)
C8—N1—C9	124.34 (19)	C6—C7—C8	129.9 (2)
O1—C1—N1	124.2 (2)	C2—C7—C8	108.30 (19)
O1—C1—C2	129.2 (2)	O2—C8—N1	124.7 (2)
N1—C1—C2	106.63 (19)	O2—C8—C7	129.4 (2)
C3—C2—C7	121.0 (2)	N1—C8—C7	105.87 (19)
C3—C2—C1	131.3 (2)	N1—C9—C10	112.26 (19)
C7—C2—C1	107.71 (18)	N1—C9—H9A	109.2
C2—C3—C4	117.7 (2)	C10—C9—H9A	109.2
C2—C3—H3A	121.2	N1—C9—H9B	109.2
C4—C3—H3A	121.2	C10—C9—H9B	109.2
C5—C4—C3	121.1 (2)	H9A—C9—H9B	107.9
C5—C4—H4	119.5	O3—C10—C9	112.2 (2)
C3—C4—H4	119.5	O3—C10—H10A	109.2
C4—C5—C6	121.2 (2)	C9—C10—H10A	109.2
C4—C5—H5	119.4	O3—C10—H10B	109.2
C6—C5—H5	119.4	C9—C10—H10B	109.2
C7—C6—C5	117.3 (2)	H10A—C10—H10B	107.9
C8—N1—C1—O1	177.2 (2)	C3—C2—C7—C6	−0.4 (3)
C9—N1—C1—O1	−2.2 (3)	C1—C2—C7—C6	−180.0 (2)
C8—N1—C1—C2	−1.6 (2)	C3—C2—C7—C8	−179.06 (19)
C9—N1—C1—C2	178.97 (18)	C1—C2—C7—C8	1.4 (2)
O1—C1—C2—C3	1.8 (4)	C1—N1—C8—O2	−175.5 (2)
N1—C1—C2—C3	−179.4 (2)	C9—N1—C8—O2	3.9 (3)
O1—C1—C2—C7	−178.7 (2)	C1—N1—C8—C7	2.4 (2)
N1—C1—C2—C7	0.1 (2)	C9—N1—C8—C7	−178.16 (18)
C7—C2—C3—C4	1.3 (3)	C6—C7—C8—O2	−3.0 (4)
C1—C2—C3—C4	−179.3 (2)	C2—C7—C8—O2	175.5 (2)
C2—C3—C4—C5	−1.7 (4)	C6—C7—C8—N1	179.2 (2)
C3—C4—C5—C6	1.3 (4)	C2—C7—C8—N1	−2.3 (2)
C4—C5—C6—C7	−0.4 (4)	C1—N1—C9—C10	−84.0 (3)
C5—C6—C7—C2	−0.1 (3)	C8—N1—C9—C10	96.7 (2)
C5—C6—C7—C8	178.3 (2)	N1—C9—C10—O3	−65.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.82	2.07	2.869 (2)	166

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.