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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1654.
Published online 2008 July 31. doi:  10.1107/S160053680802388X
PMCID: PMC2962252

4-Amino­phthalimide

Abstract

The mol­ecules in the title compound (systematic name: 5-aminoisoindole-1,3-dione), C8H6N2O2, are packed through N—H(...)O inter­molecular hydrogen-bonding inter­actions. Two types of hydrogen bonds are observed: one, involving the imide group, forms mol­ecular chains along the c axis and another two, involving the amino group, connect the mol­ecular chains.

Related literature

For related literature, see Paul & Samanta (2007 [triangle]).

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Object name is e-64-o1654-scheme1.jpg

Experimental

Crystal data

  • C8H6N2O2
  • M r = 162.15
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1654-efi8.jpg
  • a = 14.5786 (19) Å
  • b = 13.0728 (17) Å
  • c = 3.7216 (5) Å
  • V = 709.27 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.25 × 0.08 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.97, T max = 0.99
  • 7856 measured reflections
  • 978 independent reflections
  • 636 reflections with I > 2σ(I)
  • R int = 0.086

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.126
  • S = 1.09
  • 978 reflections
  • 109 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802388X/bg2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802388X/bg2195Isup2.hkl

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

Acknowledgments

MS thanks the National Institute of Science Education and Research (NISER), Bhubaneswar for financial support. The structure determination was performed at the National Single Crystal Diffractometer Facility (funded by the DST), School of Chemistry, University of Hyderabad.

supplementary crystallographic information

Comment

Fluorescent electron donor-acceptor (EDA) systems, 4-aminophthalimide and its derivatives in particular, are found to be attractive candidates for the study of various photophysical processes both in conventional and non-conventional media. Very recently, 4-aminophthalimide has been used in order to investigate specific hydrogen bonding interactions in the solvation and rotational dynamics in room temperature ionic liquids (Paul and Samanta, 2007). Since the ground state structure also influences considerably the photophysical properties of the EDA molecules, we have determined the crystal structure of the title compound C8H6N2O2, (I), shown in Fig. 1. We observe that the imide group forms N—H···O hydrogen bonds (Table 1) in a helical pattern to form molecular chains along c axis (Figure 2). The molecules in the chains are further stabilized by π-π stacking (centroid-to-centroid distance = 3.722 Å). These chains are connected through another type of N—H···O hydrogen bonds (Table 1) involving the amino hydrogen and the unused oxygen of the phthalimide group (Figure 3).

Experimental

The title compound was purchased from Aldrich. Tiny single crystals suitable for X-ray diffraction were obtained by slow evaporation from a solution of the compound in ethanol:water (9:1).

Refinement

All H atoms were placed geometrically at idealized positions and refined in the riding-model approximation with the follwing constraints: C–H = 0.93 Å, N–H = 0.86 Å and with Uiso(H) = 1.2Ueq(C),Uiso(H) = 1.2Ueq(N). In the abscense of any significant anomalous effect, the data set was merged.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.
Fig. 2.
Molecular chain along the c axis.
Fig. 3.
Packing diagram showing N—H···O intermolecular hydrogen bonds. [(1) N1—H1···O1a, (2) N1b– H1b···O1, (3) N2c—H2Ac···O2, (4) ...

Crystal data

C8H6N2O2F000 = 336
Mr = 162.15Dx = 1.518 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 704 reflections
a = 14.5786 (19) Åθ = 2.8–18.3º
b = 13.0728 (17) ŵ = 0.11 mm1
c = 3.7216 (5) ÅT = 298 K
V = 709.27 (16) Å3Needle, yellow
Z = 40.25 × 0.08 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer978 independent reflections
Radiation source: fine-focus sealed tube636 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.086
T = 298 Kθmax = 28.3º
phi and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −19→19
Tmin = 0.97, Tmax = 0.99k = −17→17
7856 measured reflectionsl = −4→4

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1098P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
978 reflectionsΔρmax = 0.22 e Å3
109 parametersΔρmin = −0.17 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/Ueq
O10.60766 (19)0.53133 (19)1.0695 (10)0.0556 (10)
O20.41159 (18)0.7846 (2)1.4175 (11)0.0559 (9)
N10.4932 (2)0.6407 (2)1.2599 (11)0.0445 (9)
H10.45420.59541.32840.053*
N20.6919 (2)1.0180 (2)0.8617 (13)0.0599 (12)
H2A0.65511.06690.91640.072*
H2B0.74431.03150.76630.072*
C10.5777 (3)0.6181 (3)1.1116 (14)0.0411 (10)
C20.7055 (3)0.7394 (3)0.8804 (12)0.0400 (10)
H20.74590.68750.81530.048*
C30.7288 (3)0.8405 (3)0.8309 (11)0.0423 (11)
H30.78570.85690.73380.051*
C40.6676 (3)0.9196 (3)0.9256 (12)0.0386 (10)
C50.5831 (3)0.8952 (3)1.0800 (12)0.0359 (10)
H50.54240.94641.14890.043*
C60.4787 (3)0.7455 (3)1.2853 (12)0.0402 (10)
C70.5613 (2)0.7937 (3)1.1281 (12)0.0346 (9)
C80.6212 (3)0.7165 (3)1.0282 (11)0.0350 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.054 (2)0.0267 (15)0.086 (3)0.0020 (13)−0.0039 (19)−0.0037 (18)
O20.0478 (17)0.0435 (17)0.076 (2)0.0027 (14)0.0124 (18)0.0012 (19)
N10.0401 (19)0.0284 (17)0.065 (2)−0.0068 (15)0.0033 (19)0.005 (2)
N20.056 (2)0.038 (2)0.086 (3)−0.0050 (17)0.012 (3)0.001 (2)
C10.042 (2)0.033 (2)0.049 (3)−0.0026 (19)−0.005 (2)0.000 (2)
C20.039 (2)0.037 (2)0.044 (3)0.0043 (17)0.002 (2)−0.002 (2)
C30.045 (2)0.039 (2)0.043 (3)−0.0019 (18)0.002 (2)0.001 (2)
C40.040 (2)0.034 (2)0.041 (2)−0.0048 (17)−0.003 (2)0.002 (2)
C50.041 (2)0.025 (2)0.041 (2)0.0078 (16)−0.004 (2)−0.003 (2)
C60.039 (2)0.036 (2)0.047 (3)0.0022 (18)−0.002 (2)−0.001 (2)
C70.035 (2)0.033 (2)0.036 (2)−0.0011 (16)−0.0067 (19)0.0014 (19)
C80.040 (2)0.030 (2)0.035 (3)0.0012 (18)−0.0032 (18)0.0008 (19)

Geometric parameters (Å, °)

O1—C11.226 (4)C2—C81.380 (5)
O2—C61.209 (4)C2—H20.9300
N1—C11.381 (5)C3—C41.411 (5)
N1—C61.389 (5)C3—H30.9300
N1—H10.8600C4—C51.396 (5)
N2—C41.356 (5)C5—C71.377 (5)
N2—H2A0.8600C5—H50.9300
N2—H2B0.8600C6—C71.479 (5)
C1—C81.467 (5)C7—C81.385 (5)
C2—C31.378 (6)
C1—N1—C6112.0 (3)N2—C4—C5121.3 (4)
C1—N1—H1124.0N2—C4—C3119.0 (4)
C6—N1—H1124.0C5—C4—C3119.6 (3)
C4—N2—H2A120.0C7—C5—C4118.5 (3)
C4—N2—H2B120.0C7—C5—H5120.8
H2A—N2—H2B120.0C4—C5—H5120.8
O1—C1—N1124.6 (4)O2—C6—N1124.6 (4)
O1—C1—C8129.0 (4)O2—C6—C7129.8 (4)
N1—C1—C8106.4 (3)N1—C6—C7105.6 (3)
C3—C2—C8118.8 (4)C5—C7—C8121.5 (4)
C3—C2—H2120.6C5—C7—C6130.5 (4)
C8—C2—H2120.6C8—C7—C6108.0 (3)
C2—C3—C4120.9 (4)C2—C8—C7120.7 (3)
C2—C3—H3119.5C2—C8—C1131.3 (4)
C4—C3—H3119.5C7—C8—C1108.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.092.924 (4)164
N2—H2B···O1ii0.862.283.122 (5)167
N2—H2A···O2iii0.862.172.996 (4)161

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+3/2, y+1/2, z−1/2; (iii) −x+1, −y+2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2195).

References

  • Bruker (1997). SAINT andSMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Paul, A. & Samanta, A. (2007). J. Phys. Chem. B, 111, 4724–4731. [PubMed]
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography