Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007691/qa0309sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007691/qa0309Isup2.hkl |
CCDC reference: 147695
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.
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.
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.
C11H10INO2 | F(000) = 608 |
Mr = 315.10 | Dx = 1.879 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.582 (1) Å | Cell parameters from 25 reflections |
b = 19.190 (3) Å | θ = 7–16° |
c = 8.143 (1) Å | µ = 2.85 mm−1 |
β = 109.95 (1)° | T = 293 K |
V = 1113.7 (3) Å3 | Transparent cubes, colourless |
Z = 4 | 0.18 × 0.18 × 0.18 mm |
Siemens R3m/V diffractometer | 1784 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 26.0°, θmin = 2.1° |
ω/2θ scans | h = 0→9 |
Absorption correction: multi-scan (Sheldrick, 1991) | k = 0→22 |
Tmin = 0.560, Tmax = 0.589 | l = −10→9 |
2350 measured reflections | 2 standard reflections every 98 reflections |
2186 independent reflections | intensity decay: ≤1% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.14 | Calculated w = 1/[σ2(Fo2) + (0.044P)2 + 1.5252P] where P = (Fo2 + 2Fc2)/3 |
2186 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C11H10INO2 | V = 1113.7 (3) Å3 |
Mr = 315.10 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.582 (1) Å | µ = 2.85 mm−1 |
b = 19.190 (3) Å | T = 293 K |
c = 8.143 (1) Å | 0.18 × 0.18 × 0.18 mm |
β = 109.95 (1)° |
Siemens R3m/V diffractometer | 1784 reflections with I > 2σ(I) |
Absorption correction: multi-scan (Sheldrick, 1991) | Rint = 0.023 |
Tmin = 0.560, Tmax = 0.589 | 2 standard reflections every 98 reflections |
2350 measured reflections | intensity decay: ≤1% |
2186 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.36 e Å−3 |
2186 reflections | Δρmin = −0.30 e Å−3 |
136 parameters |
x | y | z | Uiso*/Ueq | ||
I | 0.08683 (5) | 0.20244 (2) | 0.37612 (5) | 0.0556 (2) | |
N | 0.6980 (5) | 0.1062 (2) | 0.7787 (5) | 0.0436 (9) | |
O1 | 0.7319 (6) | 0.0120 (2) | 0.6180 (5) | 0.0629 (10) | |
O2 | 0.6748 (6) | 0.1753 (2) | 1.0041 (5) | 0.0623 (10) | |
C1 | 0.6968 (6) | 0.1194 (2) | 0.9469 (6) | 0.0437 (11) | |
C2 | 0.7286 (6) | 0.0510 (2) | 1.0383 (6) | 0.0372 (9) | |
C3 | 0.7475 (7) | 0.0334 (3) | 1.2088 (6) | 0.0481 (11) | |
H3A | 0.7327 | 0.0680 | 1.2882 | 0.080* | |
C4 | 0.7877 (8) | −0.0350 (3) | 1.2588 (7) | 0.0540 (13) | |
H4A | 0.8017 | −0.0485 | 1.3760 | 0.080* | |
C5 | 0.8064 (7) | −0.0839 (3) | 1.1414 (7) | 0.0518 (12) | |
H5A | 0.8354 | −0.1311 | 1.1800 | 0.080* | |
C6 | 0.7849 (7) | −0.0672 (3) | 0.9703 (7) | 0.0480 (11) | |
H6A | 0.7957 | −0.1017 | 0.8890 | 0.080* | |
C7 | 0.7472 (6) | 0.0009 (2) | 0.9208 (6) | 0.0366 (9) | |
C8 | 0.7250 (7) | 0.0359 (3) | 0.7531 (6) | 0.0451 (11) | |
C9 | 0.6903 (7) | 0.1592 (3) | 0.6459 (7) | 0.0537 (13) | |
H9A | 0.7846 | 0.1484 | 0.5956 | 0.080* | |
H9B | 0.7193 | 0.2040 | 0.7011 | 0.080* | |
C10 | 0.4992 (7) | 0.1633 (3) | 0.5028 (6) | 0.0484 (11) | |
H10A | 0.4518 | 0.1170 | 0.4715 | 0.080* | |
H10B | 0.5099 | 0.1855 | 0.4009 | 0.080* | |
C11 | 0.3652 (8) | 0.2031 (3) | 0.5643 (7) | 0.0525 (12) | |
H11A | 0.3635 | 0.1830 | 0.6717 | 0.080* | |
H11B | 0.4084 | 0.2503 | 0.5871 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.0502 (2) | 0.0574 (2) | 0.0534 (2) | 0.0078 (2) | 0.0100 (2) | 0.0049 (2) |
N | 0.041 (2) | 0.047 (2) | 0.040 (2) | −0.003 (2) | 0.010 (2) | 0.006 (2) |
O1 | 0.078 (3) | 0.075 (3) | 0.040 (2) | 0.002 (2) | 0.027 (2) | −0.008 (2) |
O2 | 0.081 (3) | 0.039 (2) | 0.063 (2) | 0.009 (2) | 0.018 (2) | −0.005 (2) |
C1 | 0.035 (2) | 0.046 (3) | 0.046 (3) | −0.001 (2) | 0.008 (2) | −0.005 (2) |
C2 | 0.036 (2) | 0.039 (2) | 0.037 (2) | 0.001 (2) | 0.011 (2) | −0.002 (2) |
C3 | 0.053 (3) | 0.051 (3) | 0.041 (3) | 0.002 (2) | 0.017 (2) | −0.007 (2) |
C4 | 0.060 (3) | 0.059 (3) | 0.042 (3) | 0.000 (3) | 0.016 (2) | 0.007 (2) |
C5 | 0.049 (3) | 0.042 (3) | 0.065 (3) | 0.006 (2) | 0.021 (3) | 0.009 (2) |
C6 | 0.045 (3) | 0.046 (3) | 0.053 (3) | −0.002 (2) | 0.016 (2) | −0.010 (2) |
C7 | 0.033 (2) | 0.041 (2) | 0.036 (2) | −0.002 (2) | 0.012 (2) | −0.005 (2) |
C8 | 0.039 (2) | 0.053 (3) | 0.043 (3) | −0.003 (2) | 0.012 (2) | −0.002 (2) |
C9 | 0.044 (3) | 0.059 (3) | 0.055 (3) | −0.011 (2) | 0.013 (2) | 0.015 (2) |
C10 | 0.053 (3) | 0.048 (3) | 0.042 (2) | −0.001 (2) | 0.013 (2) | 0.008 (2) |
C11 | 0.059 (3) | 0.051 (3) | 0.046 (3) | −0.004 (2) | 0.015 (2) | 0.000 (2) |
I—C11 | 2.143 (6) | C2—C7 | 1.396 (6) |
N—C8 | 1.390 (6) | C3—C4 | 1.375 (7) |
N—C1 | 1.396 (6) | C4—C5 | 1.381 (8) |
N—C9 | 1.471 (6) | C5—C6 | 1.384 (7) |
O1—C8 | 1.209 (6) | C6—C7 | 1.369 (7) |
O2—C1 | 1.203 (6) | C7—C8 | 1.479 (6) |
C1—C2 | 1.487 (6) | C9—C10 | 1.521 (7) |
C2—C3 | 1.389 (6) | C10—C11 | 1.488 (8) |
C8—N—C1 | 112.0 (4) | C4—C5—C6 | 122.3 (5) |
C8—N—C9 | 122.1 (4) | C7—C6—C5 | 117.3 (4) |
C1—N—C9 | 125.7 (4) | C6—C7—C2 | 121.0 (4) |
O2—C1—N | 126.1 (5) | C6—C7—C8 | 130.7 (4) |
O2—C1—C2 | 127.8 (5) | C2—C7—C8 | 108.3 (4) |
N—C1—C2 | 106.1 (4) | O1—C8—N | 124.0 (5) |
C3—C2—C7 | 121.2 (4) | O1—C8—C7 | 129.9 (5) |
C3—C2—C1 | 131.2 (4) | N—C8—C7 | 106.1 (4) |
C7—C2—C1 | 107.5 (4) | N—C9—C10 | 112.8 (4) |
C4—C3—C2 | 117.7 (5) | C11—C10—C9 | 110.5 (5) |
C3—C4—C5 | 120.5 (5) | C10—C11—I | 112.1 (4) |
C8—N—C1—O2 | −179.4 (5) | C1—C2—C7—C6 | 177.5 (4) |
C9—N—C1—O2 | 6.1 (8) | C3—C2—C7—C8 | −178.4 (4) |
C8—N—C1—C2 | 0.8 (5) | C1—C2—C7—C8 | −0.9 (5) |
C9—N—C1—C2 | −173.7 (4) | C1—N—C8—O1 | −179.7 (5) |
O2—C1—C2—C3 | −2.5 (9) | C9—N—C8—O1 | −5.0 (7) |
N—C1—C2—C3 | 177.3 (5) | C1—N—C8—C7 | −1.3 (5) |
O2—C1—C2—C7 | −179.7 (5) | C9—N—C8—C7 | 173.4 (4) |
N—C1—C2—C7 | 0.1 (5) | C6—C7—C8—O1 | 1.4 (9) |
C7—C2—C3—C4 | 0.8 (7) | C2—C7—C8—O1 | 179.6 (5) |
C1—C2—C3—C4 | −176.1 (5) | C6—C7—C8—N | −176.9 (5) |
C2—C3—C4—C5 | −0.6 (8) | C2—C7—C8—N | 1.3 (5) |
C3—C4—C5—C6 | −0.4 (9) | C8—N—C9—C10 | 81.1 (6) |
C4—C5—C6—C7 | 1.2 (8) | C1—N—C9—C10 | −104.9 (6) |
C5—C6—C7—C2 | −1.0 (7) | N—C9—C10—C11 | 78.8 (6) |
C5—C6—C7—C8 | 177.0 (5) | C9—C10—C11—I | −174.7 (3) |
C3—C2—C7—C6 | 0.0 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.96 (1) | 2.50 (1) | 3.224 (6) | 133 (1) |
C9—H9B···O2ii | 0.96 (1) | 2.77 (1) | 3.368 (6) | 121 (1) |
C11—H11B···O2ii | 0.96 (1) | 2.74 (1) | 3.463 (7) | 133 (1) |
C4—H4A···Iiii | 0.96 (1) | 3.51 (1) | 4.260 (5) | 136 (1) |
C5—H5A···Iiv | 0.96 (1) | 3.31 (1) | 4.192 (5) | 154 (1) |
C6—H6A···Iv | 0.96 (1) | 3.24 (1) | 4.185 (5) | 168 (1) |
C9—H9B···Ivi | 0.96 (1) | 3.21 (1) | 3.969 (5) | 137 (1) |
C11—H11A···Ivii | 0.96 (1) | 3.79 (1) | 4.225 (5) | 110 (1) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y−1/2, −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 formula | C11H10INO2 |
Mr | 315.10 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.582 (1), 19.190 (3), 8.143 (1) |
β (°) | 109.95 (1) |
V (Å3) | 1113.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.85 |
Crystal size (mm) | 0.18 × 0.18 × 0.18 |
Data collection | |
Diffractometer | Siemens R3m/V diffractometer |
Absorption correction | Multi-scan (Sheldrick, 1991) |
Tmin, Tmax | 0.560, 0.589 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2350, 2186, 1784 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.092, 1.14 |
No. of reflections | 2186 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.30 |
Computer programs: P3 Diffractometer Program (Siemens, 1991), SHELXTL-Plus (Sheldrick, 1991), SHELXTL-Plus, SHELXL93 (Sheldrick, 1993), SHELXL93.
I—C11 | 2.143 (6) | O1—C8 | 1.209 (6) |
N—C8 | 1.390 (6) | O2—C1 | 1.203 (6) |
N—C1 | 1.396 (6) | C1—C2 | 1.487 (6) |
N—C9 | 1.471 (6) | C7—C8 | 1.479 (6) |
C8—N—C1 | 112.0 (4) | O1—C8—N | 124.0 (5) |
C8—N—C9 | 122.1 (4) | O1—C8—C7 | 129.9 (5) |
C1—N—C9 | 125.7 (4) | N—C8—C7 | 106.1 (4) |
O2—C1—N | 126.1 (5) | N—C9—C10 | 112.8 (4) |
O2—C1—C2 | 127.8 (5) | C10—C11—I | 112.1 (4) |
N—C1—C2 | 106.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.96 (1) | 2.495 (7) | 3.224 (6) | 132.7 (2) |
C9—H9B···O2ii | 0.96 (1) | 2.773 (6) | 3.368 (6) | 120.9 (1) |
C11—H11B···O2ii | 0.96 (1) | 2.741 (7) | 3.463 (7) | 132.5 (1) |
C4—H4A···Iiii | 0.96 (1) | 3.514 (5) | 4.260 (5) | 136.3 (1) |
C5—H5A···Iiv | 0.96 (1) | 3.308 (5) | 4.192 (5) | 153.9 (1) |
C6—H6A···Iv | 0.96 (1) | 3.241 (6) | 4.185 (5) | 168.3 (1) |
C9—H9B···Ivi | 0.96 (1) | 3.211 (5) | 3.969 (5) | 137.2 (1) |
C11—H11A···Ivii | 0.96 (1) | 3.793 (5) | 4.225 (5) | 110.4 (1) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y−1/2, −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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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 C1═O2···I = 105.2 (3)° and C11—I···O2 166.0 (2)°, close to the ideal geometry (C═O···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).