supplementary materials
N-(4-Isopropoxyphenyl)acetamide
In the molecule of the title compound, C11H15NO2, the planar acetamide unit [maximum deviation of 0.0014 (6) Å] is oriented at a dihedral angle of 19.68 (4)° with respect to the aromatic ring. An intramolecular C-H
O interaction results in the formation of a six-membered ring. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into chains along the a axis
For the preparation of the title compound, N-(4-hydroxyphenyl)acetamide (50 mmol), 2-bromopropane (75 mmol) and potassium hydroxide (100 mmol) were mixed
with ethanol (60 ml), and then the mixture was heated to reflux. Reaction
progress was monitored by TLC. After ethanol removed in vacuo and filtration,
the title compound was obtained (yield; 83.2%, m.p. 403 K). Crystals suitable
for X-ray analysis were obtained by slow evaporation of an ethyl acetate
solution.
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H =
0.93, 0.98 and 0.96 Å for aromatic, methine and methyl H, respectively, and
constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where
x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
N-(4-isopropoxyphenyl)acetamide
top
Crystal data top
| C11H15NO2 | Dx = 1.149 Mg m−3 |
| Mr = 193.24 | Melting point: 403K K |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
| a = 9.3010 (19) Å | θ = 9–12° |
| b = 7.6490 (15) Å | µ = 0.08 mm−1 |
| c = 31.394 (6) Å | T = 294 K |
| V = 2233.5 (8) Å3 | Block, colorless |
| Z = 8 | 0.30 × 0.10 × 0.10 mm |
| F(000) = 832 | |
Data collection top
Enraf–Nonius CAD-4
diffractometer | 1099 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.0000 |
| graphite | θmax = 25.3°, θmin = 1.3° |
| ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan
(North et al., 1968) | k = 0→9 |
| Tmin = 0.977, Tmax = 0.992 | l = 0→37 |
| 2026 measured reflections | 3 standard reflections every 120 min |
| 2026 independent reflections | intensity decay: 1% |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
| wR(F2) = 0.202 | w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max < 0.001 |
| 2026 reflections | Δρmax = 0.26 e Å−3 |
| 127 parameters | Δρmin = −0.23 e Å−3 |
| Primary atom site location: structure-invariant direct methods | |
Crystal data top
| C11H15NO2 | V = 2233.5 (8) Å3 |
| Mr = 193.24 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 9.3010 (19) Å | µ = 0.08 mm−1 |
| b = 7.6490 (15) Å | T = 294 K |
| c = 31.394 (6) Å | 0.30 × 0.10 × 0.10 mm |
Data collection top
Enraf–Nonius CAD-4
diffractometer | 1099 reflections with I > 2σ(I) |
Absorption correction: ψ scan
(North et al., 1968) | Rint = 0.0000 |
| Tmin = 0.977, Tmax = 0.992 | θmax = 25.3° |
| 2026 measured reflections | 3 standard reflections every 120 min |
| 2026 independent reflections | intensity decay: 1% |
Refinement top
| R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
| wR(F2) = 0.202 | Δρmax = 0.26 e Å−3 |
| S = 1.01 | Δρmin = −0.23 e Å−3 |
| 2026 reflections | Absolute structure: ? |
| 127 parameters | Flack parameter: ? |
| ? restraints | Rogers parameter: ? |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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| | x | y | z | Uiso*/Ueq | |
| N | 0.5437 (3) | 0.2110 (3) | 0.52353 (8) | 0.0516 (7) | |
| H0A | 0.4609 | 0.2564 | 0.5183 | 0.062* | |
| O1 | 0.5722 (3) | −0.0692 (3) | 0.68713 (7) | 0.0834 (8) | |
| O2 | 0.7614 (2) | 0.1579 (3) | 0.49473 (7) | 0.0665 (7) | |
| C1 | 0.5187 (7) | −0.3739 (7) | 0.67643 (15) | 0.128 (2) | |
| H1A | 0.5192 | −0.3613 | 0.6460 | 0.192* | |
| H1B | 0.4231 | −0.3546 | 0.6870 | 0.192* | |
| H1C | 0.5494 | −0.4897 | 0.6839 | 0.192* | |
| C2 | 0.6254 (7) | −0.2587 (7) | 0.74329 (13) | 0.1163 (17) | |
| H2A | 0.6915 | −0.1733 | 0.7542 | 0.175* | |
| H2B | 0.6577 | −0.3737 | 0.7510 | 0.175* | |
| H2C | 0.5318 | −0.2385 | 0.7552 | 0.175* | |
| C3 | 0.6181 (5) | −0.2437 (6) | 0.69566 (12) | 0.0810 (12) | |
| H3A | 0.7146 | −0.2607 | 0.6838 | 0.097* | |
| C4 | 0.5728 (4) | −0.0080 (4) | 0.64580 (11) | 0.0602 (9) | |
| C5 | 0.6698 (3) | −0.0586 (4) | 0.61512 (10) | 0.0589 (9) | |
| H5A | 0.7396 | −0.1415 | 0.6215 | 0.071* | |
| C6 | 0.6637 (3) | 0.0134 (4) | 0.57479 (10) | 0.0543 (8) | |
| H6A | 0.7297 | −0.0221 | 0.5543 | 0.065* | |
| C7 | 0.5608 (3) | 0.1378 (4) | 0.56435 (9) | 0.0470 (8) | |
| C8 | 0.4652 (4) | 0.1886 (5) | 0.59609 (12) | 0.0631 (10) | |
| H8A | 0.3955 | 0.2722 | 0.5900 | 0.076* | |
| C9 | 0.4712 (4) | 0.1183 (5) | 0.63610 (11) | 0.0680 (10) | |
| H9A | 0.4069 | 0.1555 | 0.6569 | 0.082* | |
| C10 | 0.6390 (3) | 0.2191 (4) | 0.49183 (10) | 0.0515 (8) | |
| C11 | 0.5892 (4) | 0.3070 (5) | 0.45170 (11) | 0.0638 (10) | |
| H11A | 0.6652 | 0.3047 | 0.4310 | 0.096* | |
| H11B | 0.5638 | 0.4260 | 0.4578 | 0.096* | |
| H11C | 0.5069 | 0.2464 | 0.4406 | 0.096* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| N | 0.0428 (13) | 0.0549 (16) | 0.0572 (16) | 0.0014 (12) | −0.0018 (11) | 0.0035 (13) |
| O1 | 0.119 (2) | 0.0703 (17) | 0.0608 (16) | 0.0233 (16) | 0.0052 (14) | 0.0019 (13) |
| O2 | 0.0471 (13) | 0.0715 (16) | 0.0808 (16) | 0.0047 (12) | 0.0103 (12) | 0.0115 (12) |
| C1 | 0.198 (6) | 0.092 (4) | 0.094 (4) | −0.034 (4) | 0.005 (4) | 0.003 (3) |
| C2 | 0.168 (5) | 0.107 (4) | 0.074 (3) | 0.024 (4) | 0.001 (3) | 0.022 (3) |
| C3 | 0.096 (3) | 0.069 (2) | 0.078 (3) | 0.014 (2) | 0.008 (2) | 0.011 (2) |
| C4 | 0.076 (2) | 0.0508 (19) | 0.054 (2) | 0.0052 (19) | −0.0027 (17) | −0.0050 (16) |
| C5 | 0.061 (2) | 0.051 (2) | 0.065 (2) | 0.0133 (17) | −0.0040 (16) | 0.0000 (17) |
| C6 | 0.0534 (18) | 0.0518 (19) | 0.058 (2) | 0.0022 (16) | 0.0051 (15) | −0.0014 (16) |
| C7 | 0.0428 (15) | 0.0439 (17) | 0.0543 (19) | −0.0027 (14) | −0.0004 (13) | −0.0027 (14) |
| C8 | 0.062 (2) | 0.057 (2) | 0.071 (2) | 0.0136 (17) | 0.0049 (17) | 0.0004 (18) |
| C9 | 0.076 (2) | 0.064 (2) | 0.063 (2) | 0.017 (2) | 0.0114 (17) | −0.0049 (19) |
| C10 | 0.0486 (17) | 0.0420 (18) | 0.064 (2) | −0.0084 (15) | 0.0008 (15) | −0.0044 (15) |
| C11 | 0.061 (2) | 0.063 (2) | 0.067 (2) | −0.0106 (18) | −0.0042 (16) | 0.0080 (18) |
Geometric parameters (Å, °) top
| N—C10 | 1.334 (4) | C4—C5 | 1.375 (4) |
| N—C7 | 1.407 (4) | C4—C9 | 1.385 (4) |
| N—H0A | 0.8600 | C5—C6 | 1.382 (4) |
| O1—C4 | 1.379 (4) | C5—H5A | 0.9300 |
| O1—C3 | 1.427 (5) | C6—C7 | 1.389 (4) |
| O2—C10 | 1.234 (4) | C6—H6A | 0.9300 |
| C1—C3 | 1.487 (6) | C7—C8 | 1.391 (4) |
| C1—H1A | 0.9600 | C8—C9 | 1.367 (5) |
| C1—H1B | 0.9600 | C8—H8A | 0.9300 |
| C1—H1C | 0.9600 | C9—H9A | 0.9300 |
| C2—C3 | 1.501 (5) | C10—C11 | 1.501 (4) |
| C2—H2A | 0.9600 | C11—H11A | 0.9600 |
| C2—H2B | 0.9600 | C11—H11B | 0.9600 |
| C2—H2C | 0.9600 | C11—H11C | 0.9600 |
| C3—H3A | 0.9800 | | |
| | | |
| C10—N—C7 | 128.5 (3) | C4—C5—C6 | 120.2 (3) |
| C10—N—H0A | 115.7 | C4—C5—H5A | 119.9 |
| C7—N—H0A | 115.7 | C6—C5—H5A | 119.9 |
| C4—O1—C3 | 119.5 (3) | C5—C6—C7 | 121.2 (3) |
| C3—C1—H1A | 109.5 | C5—C6—H6A | 119.4 |
| C3—C1—H1B | 109.5 | C7—C6—H6A | 119.4 |
| H1A—C1—H1B | 109.5 | C6—C7—C8 | 117.6 (3) |
| C3—C1—H1C | 109.5 | C6—C7—N | 124.4 (3) |
| H1A—C1—H1C | 109.5 | C8—C7—N | 118.0 (3) |
| H1B—C1—H1C | 109.5 | C9—C8—C7 | 121.5 (3) |
| C3—C2—H2A | 109.5 | C9—C8—H8A | 119.3 |
| C3—C2—H2B | 109.5 | C7—C8—H8A | 119.3 |
| H2A—C2—H2B | 109.5 | C8—C9—C4 | 120.3 (3) |
| C3—C2—H2C | 109.5 | C8—C9—H9A | 119.9 |
| H2A—C2—H2C | 109.5 | C4—C9—H9A | 119.9 |
| H2B—C2—H2C | 109.5 | O2—C10—N | 122.7 (3) |
| O1—C3—C1 | 111.3 (4) | O2—C10—C11 | 121.1 (3) |
| O1—C3—C2 | 105.8 (3) | N—C10—C11 | 116.2 (3) |
| C1—C3—C2 | 112.4 (4) | C10—C11—H11A | 109.5 |
| O1—C3—H3A | 109.1 | C10—C11—H11B | 109.5 |
| C1—C3—H3A | 109.1 | H11A—C11—H11B | 109.5 |
| C2—C3—H3A | 109.1 | C10—C11—H11C | 109.5 |
| C5—C4—O1 | 124.5 (3) | H11A—C11—H11C | 109.5 |
| C5—C4—C9 | 119.3 (3) | H11B—C11—H11C | 109.5 |
| O1—C4—C9 | 116.1 (3) | | |
| | | |
| C4—O1—C3—C1 | −65.9 (5) | C10—N—C7—C6 | −21.2 (5) |
| C4—O1—C3—C2 | 171.7 (4) | C10—N—C7—C8 | 161.2 (3) |
| C3—O1—C4—C5 | −32.2 (5) | C6—C7—C8—C9 | −0.4 (5) |
| C3—O1—C4—C9 | 150.6 (4) | N—C7—C8—C9 | 177.4 (3) |
| O1—C4—C5—C6 | −178.5 (3) | C7—C8—C9—C4 | −0.8 (5) |
| C9—C4—C5—C6 | −1.3 (5) | C5—C4—C9—C8 | 1.7 (5) |
| C4—C5—C6—C7 | 0.2 (5) | O1—C4—C9—C8 | 179.0 (3) |
| C5—C6—C7—C8 | 0.7 (5) | C7—N—C10—O2 | 0.6 (5) |
| C5—C6—C7—N | −176.9 (3) | C7—N—C10—C11 | −179.7 (3) |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0A···O2i | 0.86 | 2.01 | 2.869 (3) | 175 |
| C6—H6A···O2 | 0.93 | 2.34 | 2.892 (4) | 118 |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0A···O2i | 0.86 | 2.01 | 2.869 (3) | 175 |
| C6—H6A···O2 | 0.93 | 2.34 | 2.892 (4) | 118 |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1. |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
![[Figure 1]](./hk2659fig1thm.gif)
As part of our ongoing studies on tandutinib (Knesl et al., 2006), we report herein the crystal structure of the title compound.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C4-C9) is, of course, planar. The B (O2/N/C10/C11) moiety is also planar with a maximum deviation of -0.0014 (6) Å for C10 atom, and it is oriented with respect to ring A at a dihedral angle of 19.68 (4)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a six-membered ring C (O2/N/C6/C7/C10/H6A), having twisted conformation.
In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into chains along the a axis, in which they may be effective in the stabilization of the structure.