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The title compound, C11H11NO3, a condensation product of L-alanine and ortho-phthal­aldehyde, crystallizes in space group P212121. Intermolecular O—H...O=C and C—H...O hydrogen bonds are present with O...O and C...O distances of 2.623 (3) and 3.338 (4) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019754/cf6128sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019754/cf6128Isup2.hkl
Contains datablock I

CCDC reference: 177229

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.087
  • Data-to-parameter ratio = 7.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.40 From the CIF: _reflns_number_total 1086 Count of symmetry unique reflns 1080 Completeness (_total/calc) 100.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 6 Fraction of Friedel pairs measured 0.006 Are heavy atom types Z>Si present no 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.

Computing details top

Data collection: CAD4 (Enraf-Nonius, 1992); cell refinement: SET4 and CELDIM (Enraf-Nonius, 1992); data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid top
Crystal data top
C11H11NO3Dx = 1.403 Mg m3
Mr = 205.21Melting point: 485 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 5.1787 (5) Åθ = 9.0–18.9°
b = 9.9128 (18) ŵ = 0.10 mm1
c = 18.918 (5) ÅT = 294 K
V = 971.2 (3) Å3Plate, colourless
Z = 40.42 × 0.21 × 0.04 mm
F(000) = 432
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.024
Radiation source: X-ray tubeθmax = 25.4°, θmin = 2.1°
Graphite monochromatorh = 66
ω–2θ scansk = 1111
1803 measured reflectionsl = 2222
1086 independent reflections3 standard reflections every 240 min
866 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0513P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1086 reflectionsΔρmax = 0.15 e Å3
139 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (3)
Special details top

Geometry. Mean plane data ex-SHELXL97 for molecule (I) ############################################

-3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240)

* 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9 0.0349 (0.0046) N1 0.1198 (0.0052) O3 0.0496 (0.0044) C3 0.0324 (0.0042) C10

Rms deviation of fitted atoms = 0.0014

-3.5692(0.0050)x + 6.8088(0.0093)y + 4.3640(0.0243)z = 2.8396(0.0222)

Angle to previous plane (with approximate e.s.d.) = 1.21 (18)

* -0.0125 (0.0016) N1 * 0.0115 (0.0015) C3 * -0.0058 (0.0015) C4 * -0.0010 (0.0016) C9 * 0.0078 (0.0015) C10 0.0664 (0.0037) O3 1.6122 (0.0047) C1 0.2270 (0.0044) C2

Rms deviation of fitted atoms = 0.0088

2.4277(0.0068)x + 8.5399(0.0077)y + 3.6905(0.0250)z = 6.0406(0.0183)

Angle to previous plane (with approximate e.s.d.) = 71.72 (9)

* 0.0062 (0.0007) O1 * 0.0076 (0.0009) O2 * -0.0191 (0.0022) C1 * 0.0053 (0.0006) C2 - 0.5248 (0.0042) N1 - 2.6141 (0.0031) O3 - 1.7542 (0.0044) C3

Rms deviation of fitted atoms = 0.0111

-3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240)

Angle to previous plane (with approximate e.s.d.) = 71.61 (8)

* 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9

Rms deviation of fitted atoms = 0.0014

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2219 (4)0.3422 (2)0.70076 (9)0.0436 (5)
O20.1185 (4)0.3225 (2)0.81453 (9)0.0448 (6)
O30.1743 (4)0.00701 (19)0.79755 (9)0.0431 (5)
N10.5015 (4)0.1415 (2)0.83717 (10)0.0322 (5)
C10.2613 (6)0.2997 (3)0.76625 (14)0.0319 (6)
C20.5186 (5)0.2258 (3)0.77452 (12)0.0336 (6)
C30.3211 (5)0.0455 (2)0.84486 (13)0.0322 (6)
C40.3303 (5)0.0001 (2)0.91926 (13)0.0330 (6)
C50.1849 (6)0.0953 (3)0.95365 (15)0.0466 (8)
C60.2280 (7)0.1147 (3)1.02500 (16)0.0554 (9)
C70.4113 (7)0.0391 (3)1.05950 (15)0.0572 (9)
C80.5580 (6)0.0569 (3)1.02528 (15)0.0508 (9)
C90.5160 (5)0.0761 (3)0.95383 (13)0.0367 (6)
C100.6353 (5)0.1726 (3)0.90280 (13)0.0405 (7)
C110.6091 (6)0.1497 (3)0.70982 (14)0.0442 (8)
H10.09830.39380.70010.065*
H20.64940.29480.78440.040*
H50.06100.14540.92960.056*
H60.13300.17891.04970.067*
H70.43730.05321.10760.069*
H80.68120.10721.04950.061*
H10A0.60560.26530.91700.049*
H10B0.81950.15720.89840.049*
H11A0.77280.10820.71950.066*
H11B0.62690.21120.67090.066*
H11C0.48500.08140.69800.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0367 (11)0.0525 (12)0.0415 (11)0.0129 (11)0.0004 (9)0.0086 (9)
O20.0356 (12)0.0555 (14)0.0432 (11)0.0109 (10)0.0066 (9)0.0017 (10)
O30.0423 (12)0.0474 (11)0.0398 (10)0.0156 (12)0.0101 (10)0.0011 (9)
N10.0268 (11)0.0351 (11)0.0346 (12)0.0030 (11)0.0047 (11)0.0020 (9)
C10.0296 (14)0.0298 (14)0.0361 (14)0.0031 (12)0.0020 (13)0.0015 (11)
C20.0254 (14)0.0331 (13)0.0421 (15)0.0032 (14)0.0012 (14)0.0010 (12)
C30.0313 (15)0.0297 (14)0.0355 (13)0.0004 (12)0.0016 (13)0.0001 (11)
C40.0310 (15)0.0323 (14)0.0358 (13)0.0052 (14)0.0016 (12)0.0000 (12)
C50.0481 (19)0.0442 (16)0.0475 (17)0.0025 (15)0.0007 (16)0.0029 (14)
C60.058 (2)0.062 (2)0.0467 (17)0.0016 (19)0.0083 (18)0.0145 (15)
C70.060 (2)0.076 (2)0.0359 (16)0.014 (2)0.0000 (16)0.0101 (15)
C80.0430 (19)0.069 (2)0.0406 (16)0.0017 (17)0.0064 (15)0.0016 (15)
C90.0297 (14)0.0457 (15)0.0346 (13)0.0050 (14)0.0017 (13)0.0025 (12)
C100.0297 (15)0.0476 (16)0.0440 (15)0.0024 (15)0.0065 (13)0.0056 (13)
C110.0408 (18)0.0467 (16)0.0452 (16)0.0089 (16)0.0058 (14)0.0015 (14)
Geometric parameters (Å, º) top
O1—C11.324 (3)C8—C91.382 (4)
O2—C11.197 (3)C9—C101.493 (4)
O3—C31.235 (3)O1—H10.82
N1—C21.453 (3)C2—H20.98
N1—C31.342 (3)C5—H50.93
N1—C101.455 (3)C6—H60.93
C1—C21.528 (4)C7—H70.93
C2—C111.512 (4)C8—H80.93
C3—C41.479 (4)C10—H10A0.97
C4—C51.373 (4)C10—H10B0.97
C4—C91.385 (4)C11—H11A0.96
C5—C61.382 (4)C11—H11B0.96
C6—C71.374 (5)C11—H11C0.96
C7—C81.380 (4)
C2—N1—C3122.6 (2)C1—O1—H1109.5
C2—N1—C10123.1 (2)N1—C2—H2106.7
C3—N1—C10112.9 (2)C11—C2—H2106.7
O1—C1—O2123.9 (3)C1—C2—H2106.7
O1—C1—C2112.5 (2)C4—C5—H5121.0
O2—C1—C2123.5 (2)C6—C5—H5121.0
N1—C2—C1107.8 (2)C7—C6—H6120.0
N1—C2—C11113.1 (2)C5—C6—H6120.0
C1—C2—C11115.2 (2)C6—C7—H7118.9
O3—C3—N1124.7 (2)C8—C7—H7118.9
O3—C3—C4128.0 (2)C7—C8—H8121.1
N1—C3—C4107.3 (2)C9—C8—H8121.1
C3—C4—C5130.0 (3)N1—C10—H10A111.2
C3—C4—C9107.9 (2)C9—C10—H10A111.2
C5—C4—C9122.1 (2)N1—C10—H10B111.2
C4—C5—C6118.1 (3)C9—C10—H10B111.2
C5—C6—C7120.0 (3)H10A—C10—H10B109.1
C6—C7—C8122.3 (3)C2—C11—H11A109.5
C7—C8—C9117.8 (3)C2—C11—H11B109.5
C4—C9—C8119.8 (3)H11A—C11—H11B109.5
C4—C9—C10109.3 (2)C2—C11—H11C109.5
C8—C9—C10130.9 (3)H11A—C11—H11C109.5
N1—C10—C9102.7 (2)H11B—C11—H11C109.5
C3—N1—C2—C158.3 (3)C9—C4—C5—C60.0 (4)
C10—N1—C2—C1107.1 (3)C3—C4—C5—C6177.7 (3)
C3—N1—C2—C1170.3 (3)C4—C5—C6—C70.3 (4)
C10—N1—C2—C11124.3 (3)C5—C6—C7—C80.3 (5)
O2—C1—C2—N125.0 (4)C6—C7—C8—C90.0 (5)
O1—C1—C2—N1158.7 (2)C7—C8—C9—C40.3 (4)
O2—C1—C2—C11152.4 (3)C7—C8—C9—C10178.2 (3)
O1—C1—C2—C1131.3 (3)C5—C4—C9—C80.3 (4)
C2—N1—C3—O39.6 (4)C3—C4—C9—C8177.8 (3)
C10—N1—C3—O3176.3 (2)C5—C4—C9—C10178.6 (2)
C2—N1—C3—C4169.1 (2)C3—C4—C9—C100.5 (3)
C10—N1—C3—C42.3 (3)C3—N1—C10—C92.0 (3)
O3—C3—C4—C51.1 (5)C2—N1—C10—C9168.6 (2)
N1—C3—C4—C5179.7 (3)C8—C9—C10—N1178.9 (3)
O3—C3—C4—C9176.9 (3)C4—C9—C10—N10.8 (3)
N1—C3—C4—C91.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.802.623 (3)178
C2—H2···O2ii0.982.513.338 (4)142
C11—H11C···O30.962.583.135 (4)117
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1, y, z.
 

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