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In the title mol­ecule, C9H8N2O2, all non-H atoms are essentially coplanar. The crystal structure is stabilized by weak N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033034/lh2162sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033034/lh2162Isup2.hkl
Contains datablock I

CCDC reference: 621415

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.048
  • wR factor = 0.134
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please provide; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

5-amino-2-methylisoindoline-1,3-dione top
Crystal data top
C9H8N2O2F(000) = 368
Mr = 176.17Dx = 1.458 Mg m3
Monoclinic, P21/nMelting point = 520–522 K
Hall symbol: -p 2ynMo Kα radiation, λ = 0.71070 Å
a = 4.8300 (8) ÅCell parameters from 1905 reflections
b = 10.6480 (14) Åθ = 2.3–27.8°
c = 15.6476 (16) ŵ = 0.11 mm1
β = 94.434 (9)°T = 294 K
V = 802.35 (19) Å3Plate, colourless
Z = 40.22 × 0.20 × 0.06 mm
Data collection top
Rigaku Saturn
diffractometer
1897 independent reflections
Radiation source: rotating anode1447 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.037
Detector resolution: 7.31 pixels mm-1θmax = 27.8°, θmin = 2.3°
ω scansh = 66
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1312
Tmin = 0.972, Tmax = 0.994l = 1620
5949 measured reflections
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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0796P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1897 reflectionsΔρmax = 0.22 e Å3
128 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.144 (18)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.7796 (3)0.18705 (12)0.56914 (8)0.0512 (4)
O20.0473 (2)0.36301 (11)0.40940 (7)0.0485 (4)
N10.4035 (3)0.29483 (12)0.50533 (8)0.0390 (4)
N20.7871 (4)0.10483 (16)0.27779 (12)0.0571 (5)
C10.6120 (3)0.20412 (15)0.50848 (10)0.0373 (4)
C20.5798 (3)0.13726 (14)0.42430 (9)0.0352 (4)
C30.7279 (3)0.03899 (15)0.39413 (10)0.0403 (4)
H30.87390.00260.42760.048*
C40.6513 (3)0.00494 (15)0.31061 (10)0.0407 (4)
C50.4316 (3)0.05383 (15)0.26139 (10)0.0430 (4)
H50.38400.02540.20600.052*
C60.2858 (3)0.15205 (16)0.29304 (10)0.0425 (4)
H60.14020.18940.25990.051*
C70.3607 (3)0.19413 (14)0.37549 (9)0.0355 (4)
C80.2442 (3)0.29305 (14)0.42703 (10)0.0369 (4)
C90.3595 (4)0.38061 (18)0.57511 (11)0.0506 (5)
H9A0.20580.43490.55880.061*
H9B0.52370.43020.58770.061*
H9C0.32000.33350.62500.061*
H10.749 (4)0.120 (2)0.2195 (14)0.063 (6)*
H20.927 (6)0.136 (2)0.3055 (16)0.080 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0497 (7)0.0612 (8)0.0398 (7)0.0056 (5)0.0145 (6)0.0018 (5)
O20.0508 (7)0.0497 (7)0.0437 (7)0.0142 (5)0.0044 (5)0.0031 (5)
N10.0420 (7)0.0425 (7)0.0317 (7)0.0039 (6)0.0020 (5)0.0033 (5)
N20.0552 (10)0.0593 (10)0.0557 (10)0.0108 (8)0.0025 (8)0.0183 (8)
C10.0358 (7)0.0399 (8)0.0352 (8)0.0008 (6)0.0037 (6)0.0028 (6)
C20.0330 (7)0.0396 (8)0.0322 (7)0.0029 (6)0.0020 (6)0.0005 (6)
C30.0361 (8)0.0445 (9)0.0393 (9)0.0023 (6)0.0041 (6)0.0006 (7)
C40.0380 (8)0.0419 (9)0.0423 (9)0.0026 (7)0.0040 (7)0.0030 (7)
C50.0444 (9)0.0520 (10)0.0316 (8)0.0043 (7)0.0032 (7)0.0059 (7)
C60.0417 (8)0.0510 (10)0.0335 (8)0.0021 (7)0.0062 (7)0.0000 (7)
C70.0347 (7)0.0398 (8)0.0315 (8)0.0016 (6)0.0007 (6)0.0026 (6)
C80.0375 (8)0.0398 (8)0.0327 (8)0.0002 (6)0.0010 (6)0.0066 (6)
C90.0604 (11)0.0518 (10)0.0389 (9)0.0076 (8)0.0012 (8)0.0088 (8)
Geometric parameters (Å, º) top
O1—C11.2128 (19)C3—C41.410 (2)
O2—C81.2228 (19)C3—H30.9300
N1—C11.393 (2)C4—C51.409 (2)
N1—C81.396 (2)C5—C61.375 (2)
N1—C91.452 (2)C5—H50.9300
N2—C41.370 (2)C6—C71.387 (2)
N2—H10.93 (2)C6—H60.9300
N2—H20.84 (3)C7—C81.465 (2)
C1—C21.495 (2)C9—H9A0.9600
C2—C31.372 (2)C9—H9B0.9600
C2—C71.395 (2)C9—H9C0.9600
C1—N1—C8111.68 (13)C6—C5—C4121.76 (15)
C1—N1—C9123.84 (14)C6—C5—H5119.1
C8—N1—C9124.48 (13)C4—C5—H5119.1
C4—N2—H1116.2 (13)C5—C6—C7118.48 (15)
C4—N2—H2120.2 (17)C5—C6—H6120.8
H1—N2—H2121 (2)C7—C6—H6120.8
O1—C1—N1124.65 (15)C6—C7—C2120.10 (14)
O1—C1—C2129.50 (15)C6—C7—C8131.35 (14)
N1—C1—C2105.86 (13)C2—C7—C8108.55 (13)
C3—C2—C7122.45 (14)O2—C8—N1123.80 (14)
C3—C2—C1130.16 (14)O2—C8—C7129.71 (14)
C7—C2—C1107.38 (13)N1—C8—C7106.49 (12)
C2—C3—C4117.73 (15)N1—C9—H9A109.5
C2—C3—H3121.1N1—C9—H9B109.5
C4—C3—H3121.1H9A—C9—H9B109.5
N2—C4—C5120.14 (16)N1—C9—H9C109.5
N2—C4—C3120.39 (16)H9A—C9—H9C109.5
C5—C4—C3119.47 (15)H9B—C9—H9C109.5
C8—N1—C1—O1179.43 (15)C5—C6—C7—C20.1 (2)
C9—N1—C1—O10.4 (3)C5—C6—C7—C8178.52 (15)
C8—N1—C1—C20.69 (17)C3—C2—C7—C60.3 (2)
C9—N1—C1—C2179.52 (14)C1—C2—C7—C6179.12 (14)
O1—C1—C2—C30.8 (3)C3—C2—C7—C8178.67 (13)
N1—C1—C2—C3179.05 (15)C1—C2—C7—C81.96 (16)
O1—C1—C2—C7178.47 (16)C1—N1—C8—O2179.21 (15)
N1—C1—C2—C71.65 (16)C9—N1—C8—O21.0 (2)
C7—C2—C3—C40.3 (2)C1—N1—C8—C70.48 (17)
C1—C2—C3—C4179.49 (15)C9—N1—C8—C7179.30 (14)
C2—C3—C4—N2178.38 (15)C6—C7—C8—O20.6 (3)
C2—C3—C4—C50.9 (2)C2—C7—C8—O2178.11 (16)
N2—C4—C5—C6178.21 (16)C6—C7—C8—N1179.69 (16)
C3—C4—C5—C61.1 (2)C2—C7—C8—N11.56 (16)
C4—C5—C6—C70.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O2i0.93 (2)2.39 (2)3.252 (2)154.2 (17)
N2—H2···O1ii0.84 (3)2.39 (3)3.179 (2)156 (2)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+2, y, z+1.
 

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