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The title compound, C5H10N2O2, has twofold crystallographic symmetry. A set of four mol­ecules packs around a \overline 4 center to form a 12-membered ring that is constructed from four O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021731/fl6064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021731/fl6064Isup2.hkl
Contains datablock I

CCDC reference: 226952

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.078
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 66.82 From the CIF: _reflns_number_total 598 Count of symmetry unique reflns 372 Completeness (_total/calc) 160.75% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 226 Fraction of Friedel pairs measured 0.608 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3-PC (Siemens, 1991); cell refinement: P3-PC; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

pentane-2,4-dione dioxime top
Crystal data top
C5H10N2O2Dx = 1.229 Mg m3
Mr = 130.15Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4n2Cell parameters from 48 reflections
Hall symbol: P -4 -2nθ = 8.1–27.0°
a = 10.852 (2) ŵ = 0.80 mm1
c = 5.9751 (15) ÅT = 130 K
V = 703.7 (3) Å3Block, colorless
Z = 40.20 × 0.20 × 0.20 mm
F(000) = 280
Data collection top
Syntex P21
diffractometer
Rint = 0.022
Radiation source: normal-focus sealed tubeθmax = 66.8°, θmin = 5.8°
Graphite monochromatorh = 012
2θω scansk = 012
777 measured reflectionsl = 07
598 independent reflections2 standard reflections every 198 reflections
577 reflections with I > 2σ(I) intensity decay: <0.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028All H-atom parameters refined
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0428P)2 + 0.1006P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
598 reflectionsΔρmax = 0.13 e Å3
63 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (3)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.33898 (10)0.40570 (10)0.2077 (2)0.0345 (4)
H10.390 (2)0.383 (2)0.076 (5)0.057 (7)*
N10.31472 (12)0.52870 (11)0.1520 (3)0.0288 (4)
C10.24110 (13)0.58023 (13)0.2909 (3)0.0288 (4)
C20.18573 (18)0.51634 (19)0.4866 (3)0.0393 (5)
H2A0.122 (2)0.565 (2)0.557 (5)0.065 (8)*
H2B0.149 (2)0.436 (2)0.447 (4)0.052 (7)*
H2C0.248 (2)0.496 (3)0.597 (5)0.069 (8)*
C30.21494 (15)0.71494 (15)0.25000.0372 (6)
H30.263 (2)0.744 (2)0.121 (3)0.049 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0378 (7)0.0213 (6)0.0445 (7)0.0055 (4)0.0048 (6)0.0006 (5)
N10.0238 (6)0.0206 (7)0.0420 (8)0.0000 (5)0.0015 (6)0.0002 (5)
C10.0204 (7)0.0269 (8)0.0392 (10)0.0009 (6)0.0003 (6)0.0053 (7)
C20.0398 (10)0.0452 (11)0.0329 (10)0.0068 (9)0.0045 (8)0.0008 (9)
C30.0247 (7)0.0247 (7)0.0622 (18)0.0002 (8)0.0055 (8)0.0055 (8)
Geometric parameters (Å, º) top
O1—N11.4007 (16)C2—H2A0.97 (2)
O1—H10.99 (3)C2—H2B0.99 (2)
N1—C11.281 (2)C2—H2C0.97 (3)
C1—C21.486 (3)C3—H30.98 (2)
C1—C31.5090 (18)
N1—O1—H199.1 (14)H2A—C2—H2B107 (2)
C1—N1—O1112.30 (13)C1—C2—H2C111.2 (15)
N1—C1—C2123.95 (13)H2A—C2—H2C109 (2)
N1—C1—C3115.81 (13)H2B—C2—H2C104 (2)
C2—C1—C3120.21 (13)C1—C3—C1i113.00 (18)
C1—C2—H2A112.2 (15)C1—C3—H3109.7 (14)
C1—C2—H2B112.8 (14)C1i—C3—H3109.3 (14)
H1—O1—N1—C1175.6 (14)N1—C1—C3—C1i119.77 (15)
O1—N1—C1—C21.1 (2)C2—C1—C3—C1i62.04 (13)
O1—N1—C1—C3177.05 (13)
Symmetry code: (i) y1/2, x+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1ii0.99 (3)1.78 (3)2.767 (2)170 (2)
Symmetry code: (ii) y+1, x, z.
 

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