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The structure of the title compound, C12H16N2O3, has been established by X-ray crystallographic study. The dioxazocine ring has a chair conformation and a hydrogen bond links the O and N atoms of two adjacent carbamoyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801002203/cf6029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801002203/cf6029Isup2.hkl
Contains datablock I

CCDC reference: 159842

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.052
  • wR factor = 0.064
  • Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

Les hétérocycles saturés à six chaînons, possédant trois hétéroatomes, telle que la 1,4,2-dioxazine, ont été peu décrits dans la littérature (El Meslouhi & Petrus, 1982; Riddell et al., 1978; El Meslouhi et al., 2000; Richard et al., 1973, 1974; Fruchier et al., 1983). Leurs études structurales et conformationnelles suscitent un intérêt certain à cause de l'inversion de l'azote et du cycle à six éléments. Afin de contribuer à l'étude structurale de ce type de composés, nous avons réalisé une analyse cristallographique de la 2-carbamoyl-6-éthyl-3-phényl-2,3,5,6 - tétrahydro-1,4,2-dioxazine, (I), obtenue par action du benzaldéhyde sur le β-uréidoxyalcool, en présence de l'acide para-toluène sulfonique.

Le cycle dioxazine présente une conformation chaise classique: les atomes O1/C3/O4/C6 formant un plan (déviation r.c.m. 0.0156 Å), N2 est situé à -0.6292 (5) Å e t C5 à 0.6764 (6) Å de ce plan. Le cycle phényl C10–C15 est plan (déviation r.c.m. 0.0028 Å) et fait un angle de 62.6 (3)° avec le plan du cycle dioxazine. Le groupement carbamoyl établit une liaison hydrogène inter-moléculaire entre l'atome d'azote N9 et l'oxygène O8: distance 2.9264 (7) Å.

Experimental top

A 0,005 M de β-uréidoxyalcool dans 100 ml de benzène anhydre, on ajoute 0,005 M de benzaldéhyde en présence d'acide para-toluène sulfonique. On chauffe à reflux sous agitation, pendant 2 h. Le mélange réactionnel est laissé à température ambiante pendant une nuit. Le précipité formé est filtré et recristallisé dans l'éthanol anhydre.

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus (Mackay et al., 1999); molecular graphics: ORTEP (Johnson, 1976); software used to prepare material for publication: maXus (Mackay et al., 1999).

Figures top
[Figure 1] Fig. 1. Perspective view of the molecule showing the labelling of the atoms with displacement ellipsoids at the 50% probability level. [Please supply French version of this caption]
(I) top
Crystal data top
C12H16N2O3Z = 2
Mr = 236.26F(000) = 248
Triclinic, P1Dx = 1.265 Mg m3
a = 5.4856 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.906 (1) ÅCell parameters from 4318 reflections
c = 12.227 (1) Åθ = 1–25.5°
α = 73.429 (4)°µ = 0.09 mm1
β = 77.443 (7)°T = 298 K
γ = 78.576 (7)°Needle, colourless
V = 615.0 (1) Å30.35 × 0.15 × 0.10 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 25.6°
ϕ scansh = 06
4318 measured reflectionsk = 1112
2218 independent reflectionsl = 1415
1827 reflections with I > 3σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom, diff
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.064Weighting scheme based on measured s.u.'s w = 1/(σ2(Fo2) + 0.03Fo2)
S = 1.04(Δ/σ)max = 0.006
1827 reflectionsΔρmax = 0.26 e Å3
154 parametersΔρmin = 0.20 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C12H16N2O3γ = 78.576 (7)°
Mr = 236.26V = 615.0 (1) Å3
Triclinic, P1Z = 2
a = 5.4856 (4) ÅMo Kα radiation
b = 9.906 (1) ŵ = 0.09 mm1
c = 12.227 (1) ÅT = 298 K
α = 73.429 (4)°0.35 × 0.15 × 0.10 mm
β = 77.443 (7)°
Data collection top
KappaCCD
diffractometer
1827 reflections with I > 3σ(I)
4318 measured reflectionsRint = 0.029
2218 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052154 parameters
wR(F2) = 0.064H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
1827 reflectionsΔρmin = 0.20 e Å3
Special details top

Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case.

Refinement. Refinement on F2.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53152 (7)0.23889 (4)0.22372 (4)0.0393 (2)
O40.94699 (7)0.37529 (4)0.19767 (3)0.0354 (2)
O81.10390 (8)0.06410 (5)0.10771 (4)0.0454 (2)
N20.77961 (9)0.16291 (5)0.22503 (4)0.0345 (2)
N90.70377 (10)0.08574 (6)0.07517 (5)0.0477 (3)
C30.93914 (11)0.23168 (6)0.26545 (5)0.0335 (3)
C50.69906 (11)0.45726 (6)0.19626 (5)0.0368 (3)
C60.54479 (11)0.38205 (7)0.15118 (5)0.0414 (3)
C70.87501 (12)0.10272 (6)0.13120 (5)0.0346 (3)
C100.86905 (12)0.22307 (6)0.39386 (5)0.0378 (3)
C110.98720 (19)0.29907 (11)0.43876 (7)0.0908 (6)
C120.9425 (2)0.28934 (12)0.55535 (8)0.1101 (8)
C130.78309 (18)0.20232 (9)0.62992 (6)0.0735 (5)
C140.6669 (2)0.12700 (10)0.58675 (7)0.0853 (6)
C150.70959 (18)0.13705 (9)0.46902 (6)0.0751 (5)
C160.72913 (13)0.60545 (7)0.12261 (6)0.0480 (4)
C170.87203 (15)0.68325 (7)0.17302 (7)0.0621 (4)
H31.104820.178540.254900.05230*
H50.622060.460750.274090.05532*
H111.099030.361610.387260.11030*
H121.029540.342900.584290.12968*
H130.750270.194230.711740.09045*
H140.550590.066610.638410.10213*
H150.625640.082260.439230.09357*
H6A0.376670.433980.150660.05976*
H6B0.622460.378320.073620.05976*
H9A0.755060.032640.018270.06721*
H9B0.527960.105040.103270.06721*
H16A0.819160.599600.047180.06583*
H16B0.564230.659950.115640.06583*
H17A0.886270.776820.123520.07991*
H17B1.036060.630310.179810.07991*
H17C0.781110.690660.248260.07991*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0242 (2)0.0440 (3)0.0456 (3)0.00725 (18)0.00231 (18)0.0186 (2)
O40.0277 (2)0.0384 (2)0.0352 (2)0.00807 (17)0.00497 (17)0.00854 (19)
O80.0363 (3)0.0525 (3)0.0423 (3)0.0015 (2)0.00585 (19)0.0239 (2)
N20.0254 (3)0.0399 (3)0.0348 (3)0.0038 (2)0.0039 (2)0.0169 (2)
N90.0376 (3)0.0568 (3)0.0473 (3)0.0053 (2)0.0092 (2)0.0312 (3)
C30.0280 (3)0.0374 (3)0.0316 (3)0.0058 (2)0.0062 (2)0.0114 (3)
C50.0297 (4)0.0403 (4)0.0360 (3)0.0032 (2)0.0058 (2)0.0142 (3)
C60.0297 (4)0.0439 (4)0.0457 (4)0.0019 (3)0.0104 (3)0.0150 (3)
C70.0353 (4)0.0334 (3)0.0309 (3)0.0053 (3)0.0042 (3)0.0112 (3)
C100.0379 (4)0.0396 (3)0.0316 (3)0.0040 (3)0.0079 (3)0.0118 (3)
C110.1077 (8)0.1215 (8)0.0418 (4)0.0676 (6)0.0064 (5)0.0277 (5)
C120.1409 (10)0.1414 (10)0.0467 (5)0.0723 (8)0.0126 (6)0.0372 (6)
C130.0922 (7)0.0853 (6)0.0338 (4)0.0091 (5)0.0128 (4)0.0194 (4)
C140.1139 (8)0.0955 (7)0.0370 (4)0.0532 (6)0.0044 (4)0.0105 (4)
C150.1010 (7)0.0836 (6)0.0361 (4)0.0546 (5)0.0005 (4)0.0154 (4)
C160.0525 (5)0.0410 (4)0.0439 (4)0.0060 (3)0.0116 (3)0.0097 (3)
C170.0722 (6)0.0416 (4)0.0660 (5)0.0160 (4)0.0148 (4)0.0135 (4)
Geometric parameters (Å, º) top
O1—N21.4198 (6)C5—C61.5040 (8)
O1—C61.4486 (7)C5—C161.5068 (8)
O4—C31.4313 (7)C10—C111.3682 (9)
O4—C51.4402 (7)C10—C151.3546 (9)
O8—C71.2334 (7)C11—C121.3713 (11)
N2—C31.4459 (7)C12—C131.3576 (12)
N2—C71.3968 (7)C13—C141.3419 (11)
N9—C71.3373 (7)C14—C151.3849 (10)
C3—C101.5147 (8)C16—C171.5194 (9)
N2—O1—C6109.20 (4)O8—C7—N2119.75 (5)
C3—O4—C5112.25 (4)O8—C7—N9124.28 (5)
O1—N2—C3112.51 (4)N2—C7—N9115.90 (5)
O1—N2—C7114.09 (4)C3—C10—C11118.20 (6)
C3—N2—C7120.23 (5)C3—C10—C15124.17 (6)
O4—C3—N2110.84 (4)C11—C10—C15117.47 (6)
O4—C3—C10111.86 (4)C10—C11—C12120.94 (8)
N2—C3—C10113.26 (5)C11—C12—C13121.07 (8)
O4—C5—C6107.81 (4)C12—C13—C14118.42 (7)
O4—C5—C16107.82 (5)C13—C14—C15120.85 (8)
C6—C5—C16113.42 (5)C10—C15—C14121.24 (7)
O1—C6—C5110.35 (5)C5—C16—C17112.80 (5)

Experimental details

Crystal data
Chemical formulaC12H16N2O3
Mr236.26
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)5.4856 (4), 9.906 (1), 12.227 (1)
α, β, γ (°)73.429 (4), 77.443 (7), 78.576 (7)
V3)615.0 (1)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.15 × 0.10
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 3σ(I)] reflections
4318, 2218, 1827
Rint0.029
(sin θ/λ)max1)0.607
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.064, 1.04
No. of reflections1827
No. of parameters154
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.20

Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), maXus (Mackay et al., 1999), ORTEP (Johnson, 1976).

 

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