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In the mol­ecule of the title compound, C11H10INO2, the phthal­imide group is not exactly planar. The dihedral angle between the mean planes of the phthal­imide and iodo­propyl moieties is 76.6 (2)°. The structure is stabilized by intermolecular C-H...O and C-H...I interactions, and an intermolecular I...O interaction of 3.571 (4) Å, the latter linking the mol­ecules into infinite chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007691/qa0309sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007691/qa0309Isup2.hkl
Contains datablock I

CCDC reference: 147695

Comment top

N-Substituted phthalimide-containing electron-donor and electron-acceptor fragments simultaneously are an important class of aromatic derivatives used in the synthesis of heat-resistant polymers (Magomedova et al., 1980, 1981), many biological derivatives (Ribar et al., 1974, 1976; Geita et al., 1970; Benetollo et al.,, 1993) and inclusion compounds (Herbstein & Kaftory, 1981; Kaftory, 1978). Their geometrical features play an important role in the synthesis process, and the X-ray analysis of the title compound, N-(3-iodopropyl)phthalimide, (I), is a further step towards understanding their structural features, the effect of the substituents and the conformation changes in this class of compounds.

The phthalimide moiety is not exactly planar, the dihedral angle between the mean planes of the two individual rings being 2.8 (2)°. The iodopropyl and phthalimide groups are folded towards each other, making an angle of 76.6 (2)°, which is in good agreement with the corresponding angles found in 4-phthalimidobutanoic acid (67.4 and 65.5°; Feeder & Jones, 1996a) and 4-phthalimidoperoxybutanoic acid (82.8°; Feeder & Jones, 1996b).

An extensive three-dimensional network of C—H···I as well as C—H···O interactions are present in the structure, involving phenyl as well as propane C—H groups. An interesting feature of the title compound is the short intermolecular O···I contacts. The intermolecular I···O2i distance is found to be 3.571 (4) Å [symmetry code: (i) x − 1, y, z − 1], which is slightly shorter than the O···I van der Waals sum of 3.67 Å (Bondi, 1964). Such oxygen–halogen interactions have been observed in many other structures (Hassel & Romming, 1962, 1967; Cody & Murray-Rust, 1984; Murray-Rust & Motherwell, 1979; Ramasubbu et al., 1986). These O···I interactions link the molecule to form chains along the c axis, with the layers of the molecules plane-to-plane stacked in `centrosymmetric dimers' and the maximum distance between the atoms in each plane being 3.8 Å. The intermolecular angles are C1O2···I = 105.2 (3)° and C11—I···O2 166.0 (2)°, close to the ideal geometry (CO···I = 120° and R—I···O=180°) which has been proposed for this type of association (Leser & Rabinovich, 1978). Similar interactions have been reported for the structure of N,N-diiodoformamide (Pritzkow, 1974).

Experimental top

The title compound was prepared as follows: 10 g of phthalimide (0.068 mol), 5.6 g of potassium carbonate and aliquat (catalytic amount) were taken in dry acetone and refluxed for 24 h, then 11.22 g of sodium iodide was added and reflux continued for another 12 h. The reaction mixture was filtered and concentrated. The product was recrystallized from ethanol.

Refinement top

H atoms were located from difference Fourier maps, positioned geometrically and included as riding atoms with fixed isotropic displacement parameters in the structure-factor calculations.

Computing details top

Data collection: P3 Diffractometer Program (Siemens, 1991); cell refinement: SHELXTL-Plus (Sheldrick, 1991); data reduction: SHELXTL-Plus; program(s) used to solve structure: SHELXTL-Plus; program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); software used to prepare material for publication: SHELXL93.

Phthalimido-3-iodo propane top
Crystal data top
C11H10INO2F(000) = 608
Mr = 315.10Dx = 1.879 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.582 (1) ÅCell parameters from 25 reflections
b = 19.190 (3) Åθ = 7–16°
c = 8.143 (1) ŵ = 2.85 mm1
β = 109.95 (1)°T = 293 K
V = 1113.7 (3) Å3Transparent cubes, colourless
Z = 40.18 × 0.18 × 0.18 mm
Data collection top
Siemens R3m/V
diffractometer
1784 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 26.0°, θmin = 2.1°
ω/2θ scansh = 09
Absorption correction: multi-scan
(Sheldrick, 1991)
k = 022
Tmin = 0.560, Tmax = 0.589l = 109
2350 measured reflections2 standard reflections every 98 reflections
2186 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.14Calculated w = 1/[σ2(Fo2) + (0.044P)2 + 1.5252P]
where P = (Fo2 + 2Fc2)/3
2186 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C11H10INO2V = 1113.7 (3) Å3
Mr = 315.10Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.582 (1) ŵ = 2.85 mm1
b = 19.190 (3) ÅT = 293 K
c = 8.143 (1) Å0.18 × 0.18 × 0.18 mm
β = 109.95 (1)°
Data collection top
Siemens R3m/V
diffractometer
1784 reflections with I > 2σ(I)
Absorption correction: multi-scan
(Sheldrick, 1991)
Rint = 0.023
Tmin = 0.560, Tmax = 0.5892 standard reflections every 98 reflections
2350 measured reflections intensity decay: 1%
2186 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.14Δρmax = 0.36 e Å3
2186 reflectionsΔρmin = 0.30 e Å3
136 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I0.08683 (5)0.20244 (2)0.37612 (5)0.0556 (2)
N0.6980 (5)0.1062 (2)0.7787 (5)0.0436 (9)
O10.7319 (6)0.0120 (2)0.6180 (5)0.0629 (10)
O20.6748 (6)0.1753 (2)1.0041 (5)0.0623 (10)
C10.6968 (6)0.1194 (2)0.9469 (6)0.0437 (11)
C20.7286 (6)0.0510 (2)1.0383 (6)0.0372 (9)
C30.7475 (7)0.0334 (3)1.2088 (6)0.0481 (11)
H3A0.73270.06801.28820.080*
C40.7877 (8)0.0350 (3)1.2588 (7)0.0540 (13)
H4A0.80170.04851.37600.080*
C50.8064 (7)0.0839 (3)1.1414 (7)0.0518 (12)
H5A0.83540.13111.18000.080*
C60.7849 (7)0.0672 (3)0.9703 (7)0.0480 (11)
H6A0.79570.10170.88900.080*
C70.7472 (6)0.0009 (2)0.9208 (6)0.0366 (9)
C80.7250 (7)0.0359 (3)0.7531 (6)0.0451 (11)
C90.6903 (7)0.1592 (3)0.6459 (7)0.0537 (13)
H9A0.78460.14840.59560.080*
H9B0.71930.20400.70110.080*
C100.4992 (7)0.1633 (3)0.5028 (6)0.0484 (11)
H10A0.45180.11700.47150.080*
H10B0.50990.18550.40090.080*
C110.3652 (8)0.2031 (3)0.5643 (7)0.0525 (12)
H11A0.36350.18300.67170.080*
H11B0.40840.25030.58710.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.0502 (2)0.0574 (2)0.0534 (2)0.0078 (2)0.0100 (2)0.0049 (2)
N0.041 (2)0.047 (2)0.040 (2)0.003 (2)0.010 (2)0.006 (2)
O10.078 (3)0.075 (3)0.040 (2)0.002 (2)0.027 (2)0.008 (2)
O20.081 (3)0.039 (2)0.063 (2)0.009 (2)0.018 (2)0.005 (2)
C10.035 (2)0.046 (3)0.046 (3)0.001 (2)0.008 (2)0.005 (2)
C20.036 (2)0.039 (2)0.037 (2)0.001 (2)0.011 (2)0.002 (2)
C30.053 (3)0.051 (3)0.041 (3)0.002 (2)0.017 (2)0.007 (2)
C40.060 (3)0.059 (3)0.042 (3)0.000 (3)0.016 (2)0.007 (2)
C50.049 (3)0.042 (3)0.065 (3)0.006 (2)0.021 (3)0.009 (2)
C60.045 (3)0.046 (3)0.053 (3)0.002 (2)0.016 (2)0.010 (2)
C70.033 (2)0.041 (2)0.036 (2)0.002 (2)0.012 (2)0.005 (2)
C80.039 (2)0.053 (3)0.043 (3)0.003 (2)0.012 (2)0.002 (2)
C90.044 (3)0.059 (3)0.055 (3)0.011 (2)0.013 (2)0.015 (2)
C100.053 (3)0.048 (3)0.042 (2)0.001 (2)0.013 (2)0.008 (2)
C110.059 (3)0.051 (3)0.046 (3)0.004 (2)0.015 (2)0.000 (2)
Geometric parameters (Å, º) top
I—C112.143 (6)C2—C71.396 (6)
N—C81.390 (6)C3—C41.375 (7)
N—C11.396 (6)C4—C51.381 (8)
N—C91.471 (6)C5—C61.384 (7)
O1—C81.209 (6)C6—C71.369 (7)
O2—C11.203 (6)C7—C81.479 (6)
C1—C21.487 (6)C9—C101.521 (7)
C2—C31.389 (6)C10—C111.488 (8)
C8—N—C1112.0 (4)C4—C5—C6122.3 (5)
C8—N—C9122.1 (4)C7—C6—C5117.3 (4)
C1—N—C9125.7 (4)C6—C7—C2121.0 (4)
O2—C1—N126.1 (5)C6—C7—C8130.7 (4)
O2—C1—C2127.8 (5)C2—C7—C8108.3 (4)
N—C1—C2106.1 (4)O1—C8—N124.0 (5)
C3—C2—C7121.2 (4)O1—C8—C7129.9 (5)
C3—C2—C1131.2 (4)N—C8—C7106.1 (4)
C7—C2—C1107.5 (4)N—C9—C10112.8 (4)
C4—C3—C2117.7 (5)C11—C10—C9110.5 (5)
C3—C4—C5120.5 (5)C10—C11—I112.1 (4)
C8—N—C1—O2179.4 (5)C1—C2—C7—C6177.5 (4)
C9—N—C1—O26.1 (8)C3—C2—C7—C8178.4 (4)
C8—N—C1—C20.8 (5)C1—C2—C7—C80.9 (5)
C9—N—C1—C2173.7 (4)C1—N—C8—O1179.7 (5)
O2—C1—C2—C32.5 (9)C9—N—C8—O15.0 (7)
N—C1—C2—C3177.3 (5)C1—N—C8—C71.3 (5)
O2—C1—C2—C7179.7 (5)C9—N—C8—C7173.4 (4)
N—C1—C2—C70.1 (5)C6—C7—C8—O11.4 (9)
C7—C2—C3—C40.8 (7)C2—C7—C8—O1179.6 (5)
C1—C2—C3—C4176.1 (5)C6—C7—C8—N176.9 (5)
C2—C3—C4—C50.6 (8)C2—C7—C8—N1.3 (5)
C3—C4—C5—C60.4 (9)C8—N—C9—C1081.1 (6)
C4—C5—C6—C71.2 (8)C1—N—C9—C10104.9 (6)
C5—C6—C7—C21.0 (7)N—C9—C10—C1178.8 (6)
C5—C6—C7—C8177.0 (5)C9—C10—C11—I174.7 (3)
C3—C2—C7—C60.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.96 (1)2.50 (1)3.224 (6)133 (1)
C9—H9B···O2ii0.96 (1)2.77 (1)3.368 (6)121 (1)
C11—H11B···O2ii0.96 (1)2.74 (1)3.463 (7)133 (1)
C4—H4A···Iiii0.96 (1)3.51 (1)4.260 (5)136 (1)
C5—H5A···Iiv0.96 (1)3.31 (1)4.192 (5)154 (1)
C6—H6A···Iv0.96 (1)3.24 (1)4.185 (5)168 (1)
C9—H9B···Ivi0.96 (1)3.21 (1)3.969 (5)137 (1)
C11—H11A···Ivii0.96 (1)3.79 (1)4.225 (5)110 (1)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z1/2; (iii) x+1, y, z+2; (iv) x+1, y1/2, z+3/2; (v) x+1, y, z+1; (vi) x+1, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H10INO2
Mr315.10
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.582 (1), 19.190 (3), 8.143 (1)
β (°) 109.95 (1)
V3)1113.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.85
Crystal size (mm)0.18 × 0.18 × 0.18
Data collection
DiffractometerSiemens R3m/V
diffractometer
Absorption correctionMulti-scan
(Sheldrick, 1991)
Tmin, Tmax0.560, 0.589
No. of measured, independent and
observed [I > 2σ(I)] reflections
2350, 2186, 1784
Rint0.023
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.092, 1.14
No. of reflections2186
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.30

Computer programs: P3 Diffractometer Program (Siemens, 1991), SHELXTL-Plus (Sheldrick, 1991), SHELXTL-Plus, SHELXL93 (Sheldrick, 1993), SHELXL93.

Selected geometric parameters (Å, º) top
I—C112.143 (6)O1—C81.209 (6)
N—C81.390 (6)O2—C11.203 (6)
N—C11.396 (6)C1—C21.487 (6)
N—C91.471 (6)C7—C81.479 (6)
C8—N—C1112.0 (4)O1—C8—N124.0 (5)
C8—N—C9122.1 (4)O1—C8—C7129.9 (5)
C1—N—C9125.7 (4)N—C8—C7106.1 (4)
O2—C1—N126.1 (5)N—C9—C10112.8 (4)
O2—C1—C2127.8 (5)C10—C11—I112.1 (4)
N—C1—C2106.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.96 (1)2.495 (7)3.224 (6)132.7 (2)
C9—H9B···O2ii0.96 (1)2.773 (6)3.368 (6)120.9 (1)
C11—H11B···O2ii0.96 (1)2.741 (7)3.463 (7)132.5 (1)
C4—H4A···Iiii0.96 (1)3.514 (5)4.260 (5)136.3 (1)
C5—H5A···Iiv0.96 (1)3.308 (5)4.192 (5)153.9 (1)
C6—H6A···Iv0.96 (1)3.241 (6)4.185 (5)168.3 (1)
C9—H9B···Ivi0.96 (1)3.211 (5)3.969 (5)137.2 (1)
C11—H11A···Ivii0.96 (1)3.793 (5)4.225 (5)110.4 (1)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z1/2; (iii) x+1, y, z+2; (iv) x+1, y1/2, z+3/2; (v) x+1, y, z+1; (vi) x+1, y+1/2, z+1/2; (vii) x, y+1/2, z+1/2.
 

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