(S)-2-(1,3-Dioxoisoindolin-2-yl)propanoic acid

The title compound, C₁₁H₉NO₄, was synthesized by mixing phthalic anhydride and (S)-2-amino­propanoic acid in acetic acid. The dihedral angle between the phthalimide ring system and the O3/O4/C9/C11 plane is 86.7 (3)°. The crystal structure is stabilized by weak O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.090
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.50
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.36
           From the CIF: _reflns_number_total               1103
           Count of symmetry unique reflns         1104
           Completeness (_total/calc)             99.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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); software used to prepare material for publication: SHELXTL.

(S)-2-(1,3-Dioxoisoindolin-2-yl)propanoic acid

Crystal data

C11H9NO4	F(000) = 228
Mr = 219.19	Dx = 1.423 Mg m^−3
Monoclinic, P21	Melting point = 435–436 K
Hall symbol: p 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.4819 (15) Å	Cell parameters from 1378 reflections
b = 10.640 (3) Å	θ = 2.3–24.8°
c = 9.034 (2) Å	µ = 0.11 mm^−1
β = 103.900 (4)°	T = 294 K
V = 511.5 (2) Å^3	Block, light yellow
Z = 2	0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area detector diffractometer	1103 independent reflections
Radiation source: fine-focus sealed tube	944 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = −6→5
Tmin = 0.974, Tmax = 0.989	k = −11→13
2889 measured reflections	l = −11→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.0419P] where P = (Fo^2 + 2Fc^2)/3
1103 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.13 e Å^−3
7 restraints	Δρmin = −0.17 e Å^−3

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	0.8946 (4)	0.3147 (3)	0.6909 (3)	0.0739 (7)
O2	0.1824 (3)	0.0808 (2)	0.5412 (2)	0.0554 (5)
O3	0.2241 (4)	0.4229 (2)	0.4965 (3)	0.0613 (6)
H3	0.0848	0.4558	0.4775	0.092*
O4	0.0660 (4)	0.3203 (2)	0.2811 (3)	0.0731 (7)
N1	0.5267 (4)	0.21070 (18)	0.5807 (2)	0.0406 (5)
C1	0.7393 (5)	0.2375 (3)	0.6992 (3)	0.0486 (6)
C2	0.7234 (5)	0.1512 (3)	0.8256 (3)	0.0463 (6)
C3	0.8876 (6)	0.1343 (3)	0.9662 (3)	0.0615 (8)
H3A	1.0317	0.1831	0.9970	0.074*
C4	0.8289 (6)	0.0417 (4)	1.0594 (3)	0.0661 (9)
H4	0.9367	0.0273	1.1543	0.079*
C5	0.6139 (7)	−0.0297 (3)	1.0144 (3)	0.0630 (8)
H5	0.5811	−0.0921	1.0791	0.076*
C6	0.4449 (6)	−0.0105 (3)	0.8745 (3)	0.0541 (7)
H6	0.2970	−0.0567	0.8457	0.065*
C7	0.5062 (4)	0.0798 (2)	0.7805 (3)	0.0427 (6)
C8	0.3776 (5)	0.1188 (2)	0.6232 (3)	0.0405 (6)
C9	0.4810 (5)	0.2675 (2)	0.4290 (3)	0.0400 (6)
H9	0.6128	0.3305	0.4326	0.048*
C10	0.5030 (6)	0.1730 (3)	0.3077 (3)	0.0553 (7)
H10A	0.6698	0.1386	0.3307	0.083*
H10B	0.4696	0.2138	0.2101	0.083*
H10C	0.3836	0.1066	0.3052	0.083*
C11	0.2314 (5)	0.3371 (2)	0.3928 (3)	0.0423 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0645 (14)	0.0808 (16)	0.0694 (13)	−0.0359 (13)	0.0024 (11)	−0.0006 (13)
O2	0.0469 (10)	0.0527 (11)	0.0598 (12)	−0.0169 (10)	−0.0008 (8)	0.0049 (9)
O3	0.0471 (11)	0.0579 (13)	0.0760 (14)	0.0085 (10)	0.0090 (10)	−0.0187 (11)
O4	0.0587 (13)	0.0706 (14)	0.0747 (15)	0.0160 (12)	−0.0139 (12)	−0.0175 (13)
N1	0.0382 (11)	0.0346 (11)	0.0460 (12)	−0.0044 (9)	0.0041 (9)	−0.0019 (9)
C1	0.0420 (14)	0.0497 (16)	0.0521 (15)	−0.0070 (13)	0.0072 (11)	−0.0121 (12)
C2	0.0435 (14)	0.0498 (15)	0.0436 (13)	0.0016 (12)	0.0065 (11)	−0.0082 (12)
C3	0.0538 (16)	0.077 (2)	0.0486 (16)	−0.0050 (16)	0.0035 (13)	−0.0077 (15)
C4	0.0686 (19)	0.083 (2)	0.0422 (15)	0.0116 (19)	0.0033 (13)	−0.0028 (16)
C5	0.079 (2)	0.063 (2)	0.0474 (15)	0.0050 (18)	0.0158 (15)	0.0085 (15)
C6	0.0610 (17)	0.0490 (15)	0.0511 (15)	−0.0017 (14)	0.0114 (13)	0.0011 (14)
C7	0.0461 (14)	0.0382 (13)	0.0428 (13)	0.0012 (12)	0.0084 (11)	−0.0069 (11)
C8	0.0394 (12)	0.0330 (12)	0.0466 (13)	−0.0020 (11)	0.0053 (10)	−0.0038 (10)
C9	0.0361 (12)	0.0344 (12)	0.0482 (14)	−0.0013 (10)	0.0075 (10)	0.0030 (11)
C10	0.0604 (18)	0.0528 (17)	0.0524 (16)	0.0106 (14)	0.0132 (13)	−0.0020 (13)
C11	0.0408 (13)	0.0327 (13)	0.0523 (14)	−0.0030 (11)	0.0089 (12)	0.0016 (11)

Geometric parameters (Å, º)

O1—C1	1.198 (3)	C4—C5	1.379 (5)
O2—C8	1.216 (3)	C4—H4	0.9300
O3—C11	1.315 (3)	C5—C6	1.392 (4)
O3—H3	0.8200	C5—H5	0.9300
O4—C11	1.197 (3)	C6—C7	1.376 (4)
N1—C8	1.386 (3)	C6—H6	0.9300
N1—C1	1.409 (3)	C7—C8	1.486 (4)
N1—C9	1.463 (3)	C9—C10	1.513 (4)
C1—C2	1.484 (4)	C9—C11	1.521 (4)
C2—C3	1.381 (4)	C9—H9	0.9800
C2—C7	1.388 (4)	C10—H10A	0.9600
C3—C4	1.383 (5)	C10—H10B	0.9600
C3—H3A	0.9300	C10—H10C	0.9600
C11—O3—H3	109.5	C6—C7—C2	121.3 (2)
C8—N1—C1	111.5 (2)	C6—C7—C8	130.9 (2)
C8—N1—C9	124.80 (19)	C2—C7—C8	107.7 (2)
C1—N1—C9	123.5 (2)	O2—C8—N1	123.9 (2)
O1—C1—N1	124.1 (3)	O2—C8—C7	129.5 (2)
O1—C1—C2	130.3 (3)	N1—C8—C7	106.6 (2)
N1—C1—C2	105.6 (2)	N1—C9—C10	112.2 (2)
C3—C2—C7	121.5 (3)	N1—C9—C11	110.2 (2)
C3—C2—C1	130.0 (3)	C10—C9—C11	113.1 (2)
C7—C2—C1	108.5 (2)	N1—C9—H9	107.0
C2—C3—C4	117.2 (3)	C10—C9—H9	107.0
C2—C3—H3A	121.4	C11—C9—H9	107.0
C4—C3—H3A	121.4	C9—C10—H10A	109.5
C5—C4—C3	121.4 (3)	C9—C10—H10B	109.5
C5—C4—H4	119.3	H10A—C10—H10B	109.5
C3—C4—H4	119.3	C9—C10—H10C	109.5
C4—C5—C6	121.5 (3)	H10A—C10—H10C	109.5
C4—C5—H5	119.3	H10B—C10—H10C	109.5
C6—C5—H5	119.3	O4—C11—O3	123.9 (3)
C7—C6—C5	117.1 (3)	O4—C11—C9	124.6 (2)
C7—C6—H6	121.5	O3—C11—C9	111.4 (2)
C5—C6—H6	121.5
C8—N1—C1—O1	−179.0 (3)	C1—C2—C7—C8	0.1 (3)
C9—N1—C1—O1	4.9 (4)	C1—N1—C8—O2	179.1 (3)
C8—N1—C1—C2	1.7 (3)	C9—N1—C8—O2	−4.8 (4)
C9—N1—C1—C2	−174.5 (2)	C1—N1—C8—C7	−1.6 (3)
O1—C1—C2—C3	−2.1 (5)	C9—N1—C8—C7	174.5 (2)
N1—C1—C2—C3	177.2 (3)	C6—C7—C8—O2	1.7 (5)
O1—C1—C2—C7	179.6 (3)	C2—C7—C8—O2	−179.8 (3)
N1—C1—C2—C7	−1.0 (3)	C6—C7—C8—N1	−177.6 (3)
C7—C2—C3—C4	1.0 (4)	C2—C7—C8—N1	0.9 (3)
C1—C2—C3—C4	−177.0 (3)	C8—N1—C9—C10	−64.3 (3)
C2—C3—C4—C5	−0.7 (5)	C1—N1—C9—C10	111.3 (3)
C3—C4—C5—C6	−1.0 (5)	C8—N1—C9—C11	62.7 (3)
C4—C5—C6—C7	2.3 (5)	C1—N1—C9—C11	−121.7 (2)
C5—C6—C7—C2	−2.0 (4)	N1—C9—C11—O4	−126.2 (3)
C5—C6—C7—C8	176.4 (3)	C10—C9—C11—O4	0.3 (4)
C3—C2—C7—C6	0.3 (4)	N1—C9—C11—O3	56.8 (3)
C1—C2—C7—C6	178.8 (2)	C10—C9—C11—O3	−176.7 (2)
C3—C2—C7—C8	−178.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^i	0.82	1.96	2.746 (3)	162

Symmetry code: (i) −x, y+1/2, −z+1.