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The structure of the title compound, C8H14NO2P, the first of a compound containing a 1,2-buta­dienyl group bound to the phospho­rus of a 1,3,2-ox­aza­phospho­rinane ring, is reported.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004105/om6083sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004105/om60832sup2.hkl
Contains datablock 2

CCDC reference: 183790

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.092
  • Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_741 Alert C Bond Calc 0.880(15), Rep 0.88000 .... Missing s.u. N -H1N 1.555 1.555 PLAT_745 Alert C D-H Calc 0.880(15), Rep 0.88000 .... Missing s.u. N -H1N 1.555 1.555 PLAT_746 Alert C H...A Calc 2.023(18), Rep 2.02000 .... Missing s.u. H1N -O1 1.555 4.654 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.39 From the CIF: _reflns_number_total 1882 Count of symmetry unique reflns 1038 Completeness (_total/calc) 181.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 844 Fraction of Friedel pairs measured 0.813 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-(3-Methyl-1,2-butadienyl)-2-oxo-1,3,2-oxazaphosphorinane top
Crystal data top
C8H14NO2PDx = 1.336 Mg m3
Mr = 187.17Melting point: 383 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
a = 9.6912 (16) ÅCell parameters from 3122 reflections
b = 13.389 (2) Åθ = 2.6–26.4°
c = 7.1699 (12) ŵ = 0.26 mm1
V = 930.3 (3) Å3T = 193 K
Z = 4Rod, colorless
F(000) = 4000.59 × 0.09 × 0.08 mm
Data collection top
Bruker PLATFORM
diffractometer/SMART 1000 CCD detector
1882 independent reflections
Radiation source: fine-focus sealed tube1600 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.5°
ω scansh = 1212
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1616
Tmin = 0.864, Tmax = 0.980l = 88
5403 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0448P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1882 reflectionsΔρmax = 0.49 e Å3
115 parametersΔρmin = 0.23 e Å3
2 restraintsAbsolute structure: Flack (1983), 844 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (14)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

The hydrogen atoms attached to carbons were refined with fixed C—H distances and with isotropic displacement parameters 20% greater than those for their attached atoms. The amino hydrogen H1N was assigned a fixed N—H distance (0.88 Å) but its atomic coordinates and isotropic displacement parameter were otherwise allowed to freely refine.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P0.54459 (6)0.29565 (4)0.32273 (12)0.02147 (17)
O10.6080 (2)0.29395 (14)0.5081 (3)0.0299 (5)
O20.40149 (16)0.35245 (12)0.3267 (3)0.0267 (4)
N0.6323 (2)0.35457 (17)0.1644 (3)0.0248 (5)
H1N0.7139 (12)0.3288 (17)0.140 (4)0.028 (8)*
C10.5049 (3)0.1712 (2)0.2506 (4)0.0270 (6)
H10.48280.12290.34300.032*
C20.5051 (3)0.1443 (2)0.0769 (4)0.0266 (6)
C30.5084 (3)0.1250 (2)0.1005 (4)0.0264 (6)
C40.6381 (3)0.09222 (19)0.1965 (5)0.0346 (7)
H4A0.71170.08390.10400.042*
H4B0.66570.14280.28800.042*
H4C0.62180.02850.26010.042*
C50.3834 (3)0.1376 (2)0.2210 (4)0.0384 (8)
H5A0.30330.15310.14270.046*
H5B0.36620.07560.29000.046*
H5C0.39880.19230.30930.046*
C60.3385 (3)0.3794 (2)0.1510 (4)0.0332 (7)
H6A0.24940.41330.17400.040*
H6B0.32040.31840.07680.040*
C70.4334 (3)0.4478 (2)0.0445 (4)0.0308 (7)
H7A0.45370.50770.12090.037*
H7B0.38720.47020.07140.037*
C80.5673 (3)0.3953 (2)0.0045 (4)0.0282 (6)
H8A0.54850.34050.09350.034*
H8B0.63100.44310.06520.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0175 (3)0.0286 (3)0.0184 (3)0.0006 (2)0.0009 (4)0.0009 (4)
O10.0282 (11)0.0390 (11)0.0225 (11)0.0042 (9)0.0050 (9)0.0030 (10)
O20.0212 (8)0.0403 (10)0.0185 (9)0.0033 (7)0.0014 (11)0.0016 (11)
N0.0197 (12)0.0324 (13)0.0225 (13)0.0018 (10)0.0044 (11)0.0036 (10)
C10.0250 (15)0.0307 (14)0.0255 (15)0.0041 (12)0.0004 (12)0.0054 (12)
C20.0200 (13)0.0244 (15)0.0353 (17)0.0020 (12)0.0007 (12)0.0008 (12)
C30.0270 (16)0.0265 (13)0.0257 (15)0.0067 (13)0.0009 (12)0.0009 (12)
C40.0352 (15)0.0368 (14)0.0319 (19)0.0037 (11)0.0060 (15)0.0022 (16)
C50.0308 (17)0.0511 (19)0.033 (2)0.0058 (14)0.0057 (13)0.0039 (14)
C60.0221 (14)0.0496 (17)0.0278 (17)0.0107 (13)0.0035 (13)0.0007 (14)
C70.0362 (18)0.0316 (15)0.0246 (17)0.0078 (13)0.0059 (13)0.0030 (12)
C80.0317 (16)0.0312 (14)0.0217 (14)0.0012 (11)0.0023 (13)0.0018 (12)
Geometric parameters (Å, º) top
P—O11.464 (2)C4—H4B0.9800
P—O21.5819 (16)C4—H4C0.9800
P—N1.623 (2)C5—H5A0.9800
P—C11.787 (3)C5—H5B0.9800
O2—C61.445 (3)C5—H5C0.9800
N—C81.470 (4)C6—C71.507 (4)
N—H1N0.880C6—H6A0.9900
C1—C21.296 (4)C6—H6B0.9900
C1—H10.9500C7—C81.517 (4)
C2—C31.299 (4)C7—H7A0.9900
C3—C41.498 (4)C7—H7B0.9900
C3—C51.498 (4)C8—H8A0.9900
C4—H4A0.9800C8—H8B0.9900
O1—P—O2111.06 (12)C3—C5—H5B109.5
O1—P—N114.98 (12)C3—C5—H5C109.5
O1—P—C1109.79 (12)H5A—C5—H5B109.5
O2—P—N103.77 (11)H5A—C5—H5C109.5
O2—P—C1105.35 (11)H5B—C5—H5C109.5
N—P—C1111.33 (13)O2—C6—C7109.6 (2)
P—O2—C6118.32 (17)O2—C6—H6A109.7
P—N—C8122.16 (18)O2—C6—H6B109.7
P—N—H1N114.7 (17)C7—C6—H6A109.7
C8—N—H1N111.6 (19)C7—C6—H6B109.7
P—C1—C2122.4 (2)H6A—C6—H6B108.2
P—C1—H1118.8C6—C7—C8110.9 (2)
C2—C1—H1118.8C6—C7—H7A109.5
C1—C2—C3175.2 (3)C6—C7—H7B109.5
C2—C3—C4121.9 (3)C8—C7—H7A109.5
C2—C3—C5121.5 (3)C8—C7—H7B109.5
C4—C3—C5116.5 (3)H7A—C7—H7B108.0
C3—C4—H4A109.5N—C8—C7110.4 (2)
C3—C4—H4B109.5N—C8—H8A109.6
C3—C4—H4C109.5N—C8—H8B109.6
H4A—C4—H4B109.5C7—C8—H8A109.6
H4A—C4—H4C109.5C7—C8—H8B109.6
H4B—C4—H4C109.5H8A—C8—H8B108.1
C3—C5—H5A109.5
O1—P—O2—C6167.35 (18)O2—P—C1—C290.7 (3)
N—P—O2—C643.3 (2)N—P—C1—C221.2 (3)
C1—P—O2—C673.8 (2)P—O2—C6—C760.3 (3)
O1—P—N—C8157.4 (2)P—N—C8—C744.1 (3)
O2—P—N—C835.9 (2)O2—C6—C7—C863.3 (3)
C1—P—N—C876.9 (2)C6—C7—C8—N54.7 (3)
O1—P—C1—C2149.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O1i0.882.022.872 (3)162
Symmetry code: (i) x+3/2, y, z1/2.
 

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