Download citation
Download citation
link to html
The mol­ecule of the title compound, C6H7N3O3, lies on the mirror plane of the space group P21/m. The acetyl substituents adopt an anti configuration. The bond lengths and angles are as expected for a mol­ecule of this kind.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004027/lh6173sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004027/lh6173Isup2.hkl
Contains datablock I

CCDC reference: 236113

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.109
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. C3 .. 3.18 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. C3 .. 3.18 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Nicolet P3 software (Nicolet, 1980); cell refinement: Nicolet P3 software; data reduction: RDNIC (Howie, 1980); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

1,4-Diacetyl-1,2,4-triazolin-5-one top
Crystal data top
C6H7N3O3F(000) = 176
Mr = 169.15Dx = 1.505 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 14 reflections
a = 6.572 (3) Åθ = 11.0–12.0°
b = 6.199 (3) ŵ = 0.12 mm1
c = 9.463 (3) ÅT = 298 K
β = 104.54 (3)°Block, colourless
V = 373.2 (3) Å30.35 × 0.30 × 0.25 mm
Z = 2
Data collection top
Nicolet P3 four-circle
diffractometer
Rint = 0.015
Radiation source: normal-focus sealed tubeθmax = 27.6°, θmin = 2.2°
Graphite monochromatorh = 08
θ–2θ scansk = 08
1010 measured reflectionsl = 1211
944 independent reflections2 standard reflections every 50 reflections
759 reflections with I > 2σ(I) intensity decay: none
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0552P)2 + 0.0599P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
944 reflectionsΔρmax = 0.18 e Å3
76 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.087 (13)
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.

Molecule on m of space group P21/m and therefore completely planar. H in calculated positions and refined with a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.1837 (2)0.25000.67936 (18)0.0607 (5)
O20.9826 (2)0.25000.37424 (16)0.0548 (4)
O30.3322 (2)0.25000.17084 (18)0.0756 (6)
N10.8331 (2)0.25000.57448 (17)0.0397 (4)
N20.6286 (2)0.25000.59470 (18)0.0416 (4)
N30.6193 (2)0.25000.35833 (17)0.0386 (4)
C11.0092 (3)0.25000.6965 (2)0.0435 (5)
C20.9545 (3)0.25000.8395 (2)0.0604 (6)
H2A0.86270.36910.84350.091*0.50
H2B1.08040.26360.91670.091*0.50
H2C0.88500.11730.85100.091*0.50
C30.5092 (3)0.25000.4656 (2)0.0395 (5)
H30.36330.25000.44540.047*
C40.5205 (3)0.25000.2067 (2)0.0477 (5)
C50.8350 (3)0.25000.4286 (2)0.0392 (4)
C60.6558 (4)0.25000.1041 (2)0.0670 (7)
H6A0.77010.15100.13770.100*0.50
H6B0.71060.39240.09850.100*0.50
H6C0.57510.20650.00920.100*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (7)0.0870 (12)0.0635 (10)0.0000.0050 (6)0.000
O20.0345 (7)0.0772 (11)0.0572 (9)0.0000.0202 (6)0.000
O30.0426 (9)0.1226 (17)0.0541 (10)0.0000.0018 (7)0.000
N10.0251 (7)0.0501 (9)0.0435 (9)0.0000.0081 (6)0.000
N20.0250 (7)0.0514 (10)0.0503 (9)0.0000.0133 (6)0.000
N30.0287 (7)0.0437 (9)0.0421 (9)0.0000.0064 (6)0.000
C10.0302 (9)0.0498 (11)0.0475 (11)0.0000.0041 (8)0.000
C20.0456 (11)0.0862 (17)0.0458 (12)0.0000.0048 (9)0.000
C30.0268 (8)0.0432 (10)0.0483 (11)0.0000.0090 (8)0.000
C40.0433 (10)0.0532 (12)0.0424 (11)0.0000.0029 (8)0.000
C50.0287 (8)0.0421 (10)0.0466 (10)0.0000.0088 (7)0.000
C60.0626 (15)0.094 (2)0.0443 (12)0.0000.0132 (11)0.000
Geometric parameters (Å, º) top
O1—C11.198 (2)C1—C21.485 (3)
O2—C51.206 (2)C2—H2A0.9600
O3—C41.198 (3)C2—H2B0.9600
N1—C51.384 (3)C2—H2C0.9600
N1—N21.405 (2)C3—H30.9300
N1—C11.415 (2)C4—C61.472 (3)
N2—C31.276 (2)C6—H6A0.9600
N3—C31.386 (2)C6—H6B0.9600
N3—C51.406 (2)C6—H6C0.9600
N3—C41.419 (3)
C5—N1—N2112.62 (14)N2—C3—N3113.14 (15)
C5—N1—C1127.14 (15)N2—C3—H3123.4
N2—N1—C1120.23 (16)N3—C3—H3123.4
C3—N2—N1104.40 (15)O3—C4—N3117.6 (2)
C3—N3—C5107.66 (15)O3—C4—C6124.4 (2)
C3—N3—C4123.37 (15)N3—C4—C6117.92 (18)
C5—N3—C4128.97 (17)O2—C5—N1129.41 (17)
O1—C1—N1120.29 (19)O2—C5—N3128.42 (18)
O1—C1—C2125.60 (19)N1—C5—N3102.17 (15)
N1—C1—C2114.11 (16)C4—C6—H6A109.5
C1—C2—H2A109.5C4—C6—H6B109.5
C1—C2—H2B109.5H6A—C6—H6B109.5
H2A—C2—H2B109.5C4—C6—H6C109.5
C1—C2—H2C109.5H6A—C6—H6C109.5
H2A—C2—H2C109.5H6B—C6—H6C109.5
H2B—C2—H2C109.5
C5—N1—N2—C30.0C3—N3—C4—C6180.0
C1—N1—N2—C3180.0C5—N3—C4—C60.0
C5—N1—C1—O10.0N2—N1—C5—O2180.0
N2—N1—C1—O1180.0C1—N1—C5—O20.0
C5—N1—C1—C2180.0N2—N1—C5—N30.0
N2—N1—C1—C20.0C1—N1—C5—N3180.0
N1—N2—C3—N30.0C3—N3—C5—O2180.0
C5—N3—C3—N20.0C4—N3—C5—O20.0
C4—N3—C3—N2180.0C3—N3—C5—N10.0
C3—N3—C4—O30.0C4—N3—C5—N1180.0
C5—N3—C4—O3180.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.932.423.350 (3)176
Symmetry code: (i) x1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds