Synthesis and crystal structure of title compound
447
Table 1. Crystallographic Data for the 2-Propyl-5-phenyl-1,
4-dioxo-1,2,3,4,5,6,7,8-octahydro-[1,4,2]diazaphosphorino[1,2-a]
[1,3,2]benzodiazaphosphorine 3-Oxide
ppm): 5.95. Anal. calcd. for C12H16BrN2O2P:
C, 43.52; H, 4.87; N, 8.46. Found: C, 43.68; H,
5.05; N, 8.66.
Empirical formula
CCDC deposit
Color
Crystal size, mm
Crystal system
Space group
C19H20N3O3P
CCDC-1003/6076
Colorless
0.10 0.15 0.20
Monoclinic
Preparation of 2-propyl-5-phenyl-1,
4-dioxo-1,2,3,4,5,6,7,8-octahydro-[1,4,2]
diazaphosphorino[1,2-a][1,3,2]
P 2(1)/c
benzodiazaphosphorine 3-oxide
˚
Unit-cell dimensions
a = 9.7585(9) A
˚
˚
b = 21.4319(19) A
c = 17.7900(16) A
A mixture of 1-(2-bromoethyl)-3-propyl-
2,3-dihydro-1,3,2-benzodiazaphosphorin-4(1H)-
one 2-oxide (0.99 g, 3 mmol), phenyl isocyanate
(0.36 g, 3 mmol), triethylamine (0.61 g, 6 mmol),
and 30 mL dry toluene was heated at reflux for
8 h and the produced triethylamine hydrobromide
was filtered off. The solvent from the filtrate was
removed under reduced pressure and the residue
was chromatographed on a column of silica
gel using a mixture of 40% ethyl acetate/light
petroleum (b.p. 60–90 C) to elute the product.
The single crystals suitable X-ray analysis were
obtained by recrystallization from a mixture
of ethyl acetate and petroleum ether (b.p. 90–
120 C), yield 0.78 g (70.4%), m.p. 152–154 C.
Anal. calcd. for C19H20N3O3P: C, 61.79; H,
5.46; N, 11.38. Found C, 61.52; H, 5.35; N,
= 100.823(2)
3
˚
Volume, A
3654.5(6)
8
369.35
1.343
0.175
1552
Z
Formula weight
3
Density
, Mg m
calc.
1
Absorption coefficient, mm
F(000)
Diffractometer/scan
Radiation/wavelength
SMART CCD 1000
Mo K (graphite mono
chrom.)/0.71073 A
˚
Temperature, K
range for data collection, deg
Scan type
298
2
2.23–25.03
ω
Index ranges
11
h
8, 25
24, 17
15,024
k
l
21
Reflections measured
Independent/observed
reflections
Absorption correction
Refinement method
6410(R = 0.0309)
int
([I 2 (I )])
SADABS
Full-matrix least-squares
on F2
1
Data/restraints/parameters
Weight
6410/0/469
11.16. IR (KBr, cm ): 2950.5, 1669.1, 1643.4 (s,
1/[ 2(Fo2) + (0.0984P)2+
C O); 1602.7 (s, C O); 1486.6, 1398.0, 1346.2
(s, P O), 1236.7, 1213.9, 1034.0 (m, P N);
939.4, 904.7, 758.5, 701.8. EI-MS (m/z, %): 369
(7.5); 341 (41.6); 326, 312, 299 (93.2); 284,
258, 235, 207, 194, 180, 152, 132 (47.5); 104
0.7604P]
P = (Fo2 + 2Fc2)/3
1.026
R1 = 0.0534, wR2 = 0.1455
R1 = 0.0776, wR2 = 0.1657
0.844/ 0.473
Goodness of fit on F2
Final R indices [I > 2 (I )]
R indices (all data)
Largest diff. peak and hole,
1
3
˚
(69.8); 77 (100). H NMR (CDCl3/TMS, ppm;
e A
3
J, Hz): 0.96 (t, 3H, NCH2CH2CH3, JHH
=
7.4), 1.88 (m, 2H, PNCH2CH2CH3, 3.60–4.15
(m, 5H, PNCH2CH2CH3 + PNCH2CH2N +
listed in Table 1. Data were collected with
a SMART CCD 1000 area detector, using
graphite monochromatized Mo K radiation ( =
1/2
PNCH2CH2N), 4.96 (m, 1H, 1/2
PNCH2CH2N), 6.92–8.35 (m, 9H, C6H5 + C6H4.
˚
0.71073 A). The structure was solved by direct
31P NMR (CDCl3/H3PO4, ppm): 7.74 (s).
methods using SHELXS-97 package and refined
on F2 using the data (I > 2 (I)) by full-matrix
least-square procedures using SHELXL-97. All
non-hydrogen atoms were refined anisotropically.
Hydrogen atoms were located from difference
maps and then added geometrically, included in
the refinement, with Uiso fixed to 1.2 times Ueq of
Crystal structure determinations
and refinements
The crystal data, data collection, and re-
finement parameters for the title compound are