Introduction
Materials and methods
Chemicals
Sample preparation
GC–MS analysis
Direct infusion electrospray ionization mass spectrometry
NMR spectroscopy
Fourier transform infrared (FT-IR), Raman and UV-VIS spectroscopies
X-ray spectroscopy
Results
GC–MS and ESI-MS
1H and 13C NMR spectroscopy
Atom position | Carbon chemical shifts (ppm) | Proton chemical shifts (ppm) |
---|---|---|
1 | 195.60 | – |
2 | 61.64 | 5.14 (s, 1H) |
3 | 30.34 | 2.21–2.28 (m, 1H); 2.31–2.39 (m, 1H) |
4 | 22.36 | 1.98–2.02 (m, 2H) |
5 | 19.98 | 1.26–1.32 (m, 3H); 1.34–1.44 (m, 3H) (signal from protons nos. 5, 9, 10) |
6 | 13.39 | 0.81 (t, J = 6.8 Hz, 3H) |
7 | – | 8.42 (bs, 1H); 10.83 (bs, 1H) |
8 | 47.07 | 2.92 (bs, 1H); 3.23 (bs, 1H) |
9 | 26.75 | 1.26–1.32 (m, 3H); 1.34–1.44 (m, 3H) (signal from protons nos. 5, 9, 10) |
10 | 22.36 | 1.26–1.32 (m, 3H); 1.34–1.44 (m, 3H) (signal from protons nos. 5, 9, 10) |
11 | 13.46 | 0.93 (t, J = 7.3 Hz, 3H) |
12,14 | 128.85 | 7.56 (t, J = 7.6 Hz, 2H) |
13 | 134.39 | 7.70 (t, J = 7.3 Hz, 1H) |
15,17 | 129.12 | 8.02–8.04 (d, 2H) |
16 | 134.64 | – |
IR, Raman, UV-VIS spectra and melting point
X-ray studies
Chemical formula | C16H26NOCl (form A) | C16H26NOCl·0.582(C2H5OH)·0.418(H2O) (form B) |
---|---|---|
Molecular weight | 283.83 | 318.15 |
Temperature (K) | 100 | 100 |
Crystal system | Orthorhombic | Monoclinic |
Space group | P212121 | P21/c |
a (Å) | 7.4206(5) | 11.7469(2) |
b (Å) | 11.4863(9) | 7.4117(1) |
c (Å) | 19.6959(12) | 21.6645(3) |
β (o) | 90 | 100.684(2) |
V (Å3) | 1678.8(2) | 1853.51(5) |
Dx (g cm−3) | 1.123 | 1.140 |
Z | 4 | 4 |
Absorption coefficient (mm−1) | 1.95 | 1.852 |
F(000) | 616 | 693 |
Crystal size (mm) | 0.50 × 0.07 × 0.02 | 0.37 × 0.03 × 0.02 |
Data collection and structure solution: | ||
Data collected | 9242 | 12,617 |
Independent reflections | 3237 | 3685 |
Observed reflections [I > 2σ(I)] | 2780 | 3555 |
R(int.) | 0.047 | 0.019 |
Completeness (%) | 98 | 100 |
Tmax/Tmin | 1.000/0.445 | 1.000/0.741 |
No. of parameters | 175 | 202 |
R1[I > 2σ(I)] | 0.087 | 0.057 |
wR2 (all data) | 0.242 | 0.167 |
S | 1.12 | 1.07 |
Largest diff. peak and hole [e Å−3] | 1.14, − 0.63 | 1.03, − 1.06 |
CCDC | 1,963,390 | 1,963,389 |