2-[2-(1,3-Dioxoisoindolin-2-yl)acetamido]-acetic acid.

The title mol-ecule, C(12)H(10)N(2)O(5), is non-planar with dihedral angles of 89.08 (7) and 83.21 (7)° between the phthalimide and acetamide mean planes, and the acetamide and acetic acid mean planes, respectively. In the crystal, symmetry-related mol-ecules are linked via N-H⋯O and O-H⋯O hydrogen bonds, forming an undulating two-dimensional network. There are also a number of weak C-H⋯O inter-actions, leading to the formation of a three-dimensional arrangement.

Related literature

For the structures and biological properties of phthalimides and various derivatives, see: Antunes et al. (1998 ▶); Barooah & Baruah (2007 ▶); Barooah et al. (2006 ▶); Khan et al. (2002 ▶); Sharma et al. (2010 ▶); Yunus et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For bond lengths and angles in the phthalimide group, see: Feeder & Jones (1996 ▶); Ng (1992 ▶).

Experimental

Crystal data

C12H10N2O5

M = 262.22

Monoclinic,

a = 4.8195 (5) Å

b = 10.3415 (11) Å

c = 22.629 (2) Å

β = 90.17 (1)°

V = 1127.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.939, T max = 1.000

6788 measured reflections

2731 independent reflections

2533 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.07

2731 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043047/su2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043047/su2220Isup2.hkl

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

C12H10N2O5	F(000) = 544
Mr = 262.22	Dx = 1.544 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6788 reflections
a = 4.8195 (5) Å	θ = 2.7–28.3°
b = 10.3415 (11) Å	µ = 0.12 mm−1
c = 22.629 (2) Å	T = 173 K
β = 90.17 (1)°	Block, colorless
V = 1127.9 (2) Å3	0.34 × 0.24 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	2731 independent reflections
Radiation source: fine-focus sealed tube	2533 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω and φ scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.939, Tmax = 1.000	k = −6→13
6788 measured reflections	l = −29→29

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.037P)2 + 0.579P] where P = (Fo2 + 2Fc2)/3
2731 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	1.42937 (19)	0.17860 (9)	0.07903 (4)	0.0274 (3)
O2	0.7194 (2)	0.46000 (10)	0.04263 (4)	0.0338 (3)
O3	1.11056 (19)	0.36795 (9)	0.23395 (4)	0.0250 (3)
O4	0.8527 (2)	0.07998 (11)	0.31666 (4)	0.0333 (3)
O5	1.05382 (19)	0.04425 (9)	0.22876 (4)	0.0264 (3)
N1	1.0744 (2)	0.32888 (10)	0.07534 (4)	0.0205 (3)
N2	0.8077 (2)	0.25359 (10)	0.18003 (4)	0.0214 (3)
C1	1.1901 (3)	0.10108 (14)	−0.04587 (6)	0.0285 (4)
C2	1.0418 (3)	0.09730 (15)	−0.09889 (6)	0.0336 (4)
C3	0.8300 (3)	0.18476 (15)	−0.11078 (6)	0.0329 (4)
C4	0.7551 (3)	0.27995 (14)	−0.06977 (6)	0.0279 (4)
C5	0.9028 (2)	0.28280 (12)	−0.01754 (5)	0.0223 (3)
C6	1.1163 (2)	0.19590 (12)	−0.00576 (5)	0.0219 (3)
C7	1.2343 (2)	0.22725 (12)	0.05335 (5)	0.0208 (3)
C8	0.8738 (2)	0.37080 (12)	0.03419 (5)	0.0223 (3)
C9	1.1328 (2)	0.39863 (11)	0.12934 (5)	0.0206 (3)
C10	1.0158 (2)	0.33726 (11)	0.18492 (5)	0.0190 (3)
C11	0.6866 (2)	0.19718 (13)	0.23289 (6)	0.0245 (3)
C12	0.8745 (2)	0.10203 (12)	0.26443 (5)	0.0218 (3)
H1A	1.33480	0.04130	−0.03780	0.0340*
H2	0.743 (4)	0.2331 (18)	0.1435 (8)	0.037 (5)*
H2A	1.08690	0.03340	−0.12750	0.0400*
H3A	0.73430	0.17980	−0.14740	0.0390*
H4A	0.60970	0.33960	−0.07750	0.0340*
H5	1.159 (4)	−0.018 (2)	0.2480 (8)	0.043 (5)*
H9A	1.05660	0.48720	0.12570	0.0250*
H9B	1.33640	0.40630	0.13380	0.0250*
H11A	0.51250	0.15240	0.22190	0.0290*
H11B	0.63790	0.26770	0.26060	0.0290*

	U11	U22	U33	U12	U13	U23
O1	0.0269 (4)	0.0280 (5)	0.0271 (5)	0.0052 (4)	−0.0068 (4)	−0.0024 (4)
O2	0.0349 (5)	0.0362 (5)	0.0302 (5)	0.0138 (4)	−0.0064 (4)	−0.0023 (4)
O3	0.0277 (4)	0.0293 (5)	0.0180 (4)	−0.0050 (4)	−0.0041 (3)	0.0004 (3)
O4	0.0375 (5)	0.0401 (6)	0.0224 (4)	0.0032 (4)	0.0029 (4)	0.0082 (4)
O5	0.0292 (5)	0.0281 (5)	0.0218 (4)	0.0061 (4)	−0.0019 (3)	0.0023 (4)
N1	0.0219 (5)	0.0227 (5)	0.0168 (4)	0.0014 (4)	−0.0018 (4)	−0.0003 (4)
N2	0.0225 (5)	0.0223 (5)	0.0195 (5)	−0.0013 (4)	−0.0043 (4)	0.0029 (4)
C1	0.0313 (6)	0.0291 (7)	0.0251 (6)	−0.0009 (5)	0.0007 (5)	−0.0051 (5)
C2	0.0411 (7)	0.0366 (7)	0.0232 (6)	−0.0061 (6)	0.0011 (5)	−0.0094 (5)
C3	0.0370 (7)	0.0434 (8)	0.0183 (6)	−0.0096 (6)	−0.0047 (5)	−0.0007 (5)
C4	0.0281 (6)	0.0352 (7)	0.0205 (6)	−0.0041 (5)	−0.0039 (5)	0.0045 (5)
C5	0.0235 (5)	0.0254 (6)	0.0181 (5)	−0.0028 (5)	0.0002 (4)	0.0020 (4)
C6	0.0227 (5)	0.0243 (6)	0.0187 (5)	−0.0036 (4)	−0.0009 (4)	0.0002 (4)
C7	0.0219 (5)	0.0209 (5)	0.0197 (5)	−0.0021 (4)	0.0001 (4)	−0.0003 (4)
C8	0.0225 (5)	0.0260 (6)	0.0185 (5)	0.0000 (4)	−0.0014 (4)	0.0033 (4)
C9	0.0235 (5)	0.0210 (5)	0.0173 (5)	−0.0016 (4)	−0.0013 (4)	−0.0008 (4)
C10	0.0201 (5)	0.0186 (5)	0.0182 (5)	0.0028 (4)	−0.0020 (4)	0.0003 (4)
C11	0.0200 (5)	0.0275 (6)	0.0259 (6)	−0.0005 (5)	0.0012 (4)	0.0054 (5)
C12	0.0207 (5)	0.0219 (6)	0.0228 (6)	−0.0051 (4)	−0.0021 (4)	0.0021 (4)

O1—C7	1.2130 (14)	C3—C4	1.401 (2)
O2—C8	1.2008 (15)	C4—C5	1.3782 (18)
O3—C10	1.2399 (14)	C5—C8	1.4896 (17)
O4—C12	1.2086 (15)	C5—C6	1.3913 (16)
O5—C12	1.3265 (14)	C6—C7	1.4877 (16)
O5—H5	0.93 (2)	C9—C10	1.5188 (16)
N1—C8	1.4087 (14)	C11—C12	1.5146 (17)
N1—C9	1.4459 (15)	C1—H1A	0.9500
N1—C7	1.3959 (15)	C2—H2A	0.9500
N2—C10	1.3290 (14)	C3—H3A	0.9500
N2—C11	1.4546 (16)	C4—H4A	0.9500
N2—H2	0.908 (18)	C9—H9A	0.9900
C1—C2	1.395 (2)	C9—H9B	0.9900
C1—C6	1.3834 (18)	C11—H11A	0.9900
C2—C3	1.390 (2)	C11—H11B	0.9900
C12—O5—H5	112.5 (11)	O3—C10—N2	121.14 (10)
C7—N1—C9	124.79 (9)	O3—C10—C9	119.83 (10)
C8—N1—C9	122.45 (10)	N2—C11—C12	114.03 (9)
C7—N1—C8	112.00 (9)	O4—C12—O5	124.66 (11)
C10—N2—C11	119.81 (10)	O4—C12—C11	121.99 (11)
C10—N2—H2	119.0 (12)	O5—C12—C11	113.31 (10)
C11—N2—H2	121.2 (12)	C2—C1—H1A	121.00
C2—C1—C6	116.87 (13)	C6—C1—H1A	122.00
C1—C2—C3	121.49 (13)	C1—C2—H2A	119.00
C2—C3—C4	121.31 (13)	C3—C2—H2A	119.00
C3—C4—C5	116.72 (13)	C2—C3—H3A	119.00
C4—C5—C8	129.61 (11)	C4—C3—H3A	119.00
C4—C5—C6	122.03 (11)	C3—C4—H4A	122.00
C6—C5—C8	108.37 (9)	C5—C4—H4A	122.00
C1—C6—C5	121.57 (11)	N1—C9—H9A	109.00
C1—C6—C7	130.24 (11)	N1—C9—H9B	108.00
C5—C6—C7	108.18 (10)	C10—C9—H9A	108.00
N1—C7—C6	105.94 (9)	C10—C9—H9B	109.00
O1—C7—C6	129.35 (11)	H9A—C9—H9B	108.00
O1—C7—N1	124.71 (11)	N2—C11—H11A	109.00
O2—C8—N1	123.76 (11)	N2—C11—H11B	109.00
O2—C8—C5	130.84 (10)	C12—C11—H11A	109.00
N1—C8—C5	105.41 (9)	C12—C11—H11B	109.00
N1—C9—C10	114.81 (9)	H11A—C11—H11B	108.00
N2—C10—C9	119.02 (10)
C9—N1—C7—C6	−173.65 (10)	C3—C4—C5—C8	−179.94 (13)
C7—N1—C8—O2	−177.27 (11)	C3—C4—C5—C6	0.06 (19)
C9—N1—C8—O2	−6.78 (17)	C4—C5—C6—C1	−0.53 (19)
C7—N1—C8—C5	2.75 (12)	C6—C5—C8—N1	−0.90 (12)
C8—N1—C7—O1	176.11 (11)	C8—C5—C6—C7	−1.12 (12)
C9—N1—C7—O1	5.88 (18)	C4—C5—C6—C7	178.88 (11)
C8—N1—C7—C6	−3.42 (12)	C8—C5—C6—C1	179.47 (11)
C8—N1—C9—C10	104.76 (12)	C6—C5—C8—O2	179.13 (12)
C9—N1—C8—C5	173.24 (9)	C4—C5—C8—O2	−0.9 (2)
C7—N1—C9—C10	−85.99 (12)	C4—C5—C8—N1	179.11 (12)
C11—N2—C10—O3	0.39 (17)	C1—C6—C7—O1	2.6 (2)
C11—N2—C10—C9	−177.90 (10)	C5—C6—C7—O1	−176.76 (12)
C10—N2—C11—C12	−70.18 (14)	C5—C6—C7—N1	2.74 (12)
C2—C1—C6—C7	−178.78 (12)	C1—C6—C7—N1	−177.93 (12)
C2—C1—C6—C5	0.48 (19)	N1—C9—C10—O3	161.21 (10)
C6—C1—C2—C3	0.0 (2)	N1—C9—C10—N2	−20.48 (14)
C1—C2—C3—C4	−0.5 (2)	N2—C11—C12—O4	154.71 (12)
C2—C3—C4—C5	0.4 (2)	N2—C11—C12—O5	−27.42 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.908 (18)	2.172 (19)	3.0208 (13)	155.3 (17)
O5—H5···O3ii	0.93 (2)	1.67 (2)	2.5777 (13)	165.4 (17)
C2—H2A···O5iii	0.95	2.52	3.3142 (17)	141
C9—H9A···O4iv	0.99	2.56	3.2407 (15)	126
C9—H9B···O4v	0.99	2.59	3.3378 (15)	132
C11—H11A···O5i	0.99	2.48	3.4364 (14)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.908 (18)	2.172 (19)	3.0208 (13)	155.3 (17)
O5—H5⋯O3ii	0.93 (2)	1.67 (2)	2.5777 (13)	165.4 (17)
C2—H2A⋯O5iii	0.95	2.52	3.3142 (17)	141
C9—H9A⋯O4iv	0.99	2.56	3.2407 (15)	126
C9—H9B⋯O4v	0.99	2.59	3.3378 (15)	132
C11—H11A⋯O5i	0.99	2.48	3.4364 (14)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .