Home Crystal structure of 4-isobutoxybenzaldehyde oxime, C11H15NO2
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Crystal structure of 4-isobutoxybenzaldehyde oxime, C11H15NO2

  • Xian Tang and De-Cai Wang EMAIL logo
Published/Copyright: May 14, 2019

Abstract

C11H15O2N, monoclinic, P21/n (no. 14), a = 13.5152(2) Å, b = 6.19120(10) Å, c = 14.3917(2) Å, β = 115.467(2)°, V = 1087.22(3) Å3, Z = 4, Rgt(F) = 0.0384, wRref(F2) = 0.1104 T = 170(2) K.

CCDC no.: 1899040

The hydrogen bonded dimer of the title structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Source of materials

Commercially available p-hydroxybenzaldehyde (1.22 g, 10 mmol), and 1-bromo-2-methylpropane (2.72 g, 10 mmol) were dissoved in 40 mL N,N-dimethylformamide at 85 °C, and then stirring 4 h to generate 4-isobutoxybenzaldehyde. The title compound was synthesized in a second step by the reaction of 4-isobutoxybenzaldehyde and hydroxylamine (molar ratio 1:2) in ethanol. A yellow powder was obtained by extraction and evaporation. Crystals were obtained by recrystallization from n-hexan in the yield of 79°. ESI m/z = 194.11(M + 1), 1H NMR (400 MHz, DMSO-d6) δ [p.p.m.] 10.96 (s, 1H),

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.41 × 0.33 × 0.21 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.66 mm−1
Diffractometer, scan mode:XtaLAB Synergy R, ω
θmax, completeness:75.4°, 99%
N(hkl)measured, N(hkl)unique, Rint:6556, 2176, 0.011
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2061
N(param)refined:129
Programs:CrysAlisPRO [1], Olex2 [2], SHELX [3], [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
O10.02528(6)0.22943(12)0.11522(6)0.0464(2)
O20.55866(7)0.27237(16)0.04356(8)0.0620(3)
H20.5708820.3957390.0123820.093*
N10.46013(7)0.32671(16)0.04898(7)0.0459(2)
C1−0.18343(10)−0.0681(2)0.17044(10)0.0563(3)
H1A−0.142580−0.0958370.2443380.084*
H1B−0.182691−0.1979060.1318050.084*
H1C−0.259303−0.0301850.1550900.084*
C2−0.12766(12)0.3193(2)0.19971(12)0.0666(4)
H2A−0.0903470.4351330.1808480.100*
H2B−0.0881730.2893790.2735410.100*
H2C−0.2028030.3639850.1837860.100*
C3−0.13022(8)0.11786(18)0.13955(8)0.0435(3)
H3−0.1756960.1488250.0649390.052*
C4−0.01664(9)0.05442(18)0.15313(8)0.0428(3)
H4A0.0315960.0279670.2267330.051*
H4B−0.020108−0.0792760.1141050.051*
C50.12547(8)0.20846(17)0.11539(7)0.0384(2)
C60.15825(8)0.38244(17)0.07351(8)0.0428(3)
H60.1123350.5057190.0495650.051*
C70.25638(8)0.37628(18)0.06677(8)0.0423(3)
H70.2777050.4957080.0380840.051*
C80.32585(8)0.19607(17)0.10163(7)0.0396(2)
C90.29339(9)0.02768(18)0.14577(8)0.0436(3)
H90.340337−0.0936460.1717000.052*
C100.19410(9)0.03107(17)0.15325(8)0.0419(3)
H100.173575−0.0862250.1838020.050*
C110.42728(9)0.17745(19)0.08921(9)0.0468(3)
H110.4698790.0496660.1119580.056*

8.07 (s, 1H), 7.49 (d, 2H), 6.89 (d, 2H), 3.74 (d, 2H), 2.14–2.03 (m, 1H), 1.03 (d, 6H).

Experimental details

All H atoms attached to carbon were included using a riding-model, with C—H = 0.93–0.97 Å, and their Uiso values were set to 1.2Ueq or 1.5Ueq. The H atom at O2 was also included using a riding-mode, with O—H = 0.82 Å and their Uiso values were set to 1.5Ueq.

Comment

The title compound, 4-isobutoxybenzaldehyde oxime is an important drug intermediate [5], [6]. Further surveys of crystal structures containing such oxime were recently carried out [7]. To the best of our knowledge, there is no example of an isobutoxy benzaldehyde oxime that has been reported so far.

The asymmetric unit of the title structure contains one 4-isobutoxybenzaldehyde oxime molecule. The bond lengths and angles within the structure of 4-isobutoxybenzaldehyde oxime are unexceptional and lie within the expected ranges. In details, the C—O distances within 4-isobutoxybenzaldehyde oxime have values between 1.359(1)–1.434(1) Å. The N1—O2 distance is 1.408(1) Å. The N1—C11 distance is 1.276(1) Å, which suggests a N=C double bond. Two intermolecular H-bonds, O—H⋯N (dO⋯N = 2.776(2) Å; dH⋯N = 1.895(2) Å; ∠OHN = 156.14(1)°), connect neighboring molecules pairwise (cf. the figure). In total, the crystal structure of 4-isobutoxybenzaldehyde oxime could be viewed as dimers connected with each other by weak interaction for construction a three dimensional network.

Acknowledgements

The authors thank Liu Zongwen (Nanjing Tech University) for data collection.

References

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Received: 2019-03-11
Accepted: 2019-04-17
Published Online: 2019-05-14
Published in Print: 2019-09-25

©2019 Xian Tang et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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