Acetyl­acetone dioxime

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

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

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Computing details

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

Crystal data

C5H10N2O2	Dx = 1.229 Mg m^−3
Mr = 130.15	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4n2	Cell parameters from 48 reflections
Hall symbol: P -4 -2n	θ = 8.1–27.0°
a = 10.852 (2) Å	µ = 0.80 mm^−1
c = 5.9751 (15) Å	T = 130 K
V = 703.7 (3) Å^3	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm
F(000) = 280

Data collection

Syntex P21 diffractometer	Rint = 0.022
Radiation source: normal-focus sealed tube	θmax = 66.8°, θmin = 5.8°
Graphite monochromator	h = 0→12
2θ–ω scans	k = 0→12
777 measured reflections	l = 0→7
598 independent reflections	2 standard reflections every 198 reflections
577 reflections with I > 2σ(I)	intensity decay: <0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	All H-atom parameters refined
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.1006P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
598 reflections	Δρmax = 0.13 e Å^−3
63 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.33898 (10)	0.40570 (10)	0.2077 (2)	0.0345 (4)
H1	0.390 (2)	0.383 (2)	0.076 (5)	0.057 (7)*
N1	0.31472 (12)	0.52870 (11)	0.1520 (3)	0.0288 (4)
C1	0.24110 (13)	0.58023 (13)	0.2909 (3)	0.0288 (4)
C2	0.18573 (18)	0.51634 (19)	0.4866 (3)	0.0393 (5)
H2A	0.122 (2)	0.565 (2)	0.557 (5)	0.065 (8)*
H2B	0.149 (2)	0.436 (2)	0.447 (4)	0.052 (7)*
H2C	0.248 (2)	0.496 (3)	0.597 (5)	0.069 (8)*
C3	0.21494 (15)	0.71494 (15)	0.2500	0.0372 (6)
H3	0.263 (2)	0.744 (2)	0.121 (3)	0.049 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0378 (7)	0.0213 (6)	0.0445 (7)	0.0055 (4)	0.0048 (6)	0.0006 (5)
N1	0.0238 (6)	0.0206 (7)	0.0420 (8)	0.0000 (5)	0.0015 (6)	−0.0002 (5)
C1	0.0204 (7)	0.0269 (8)	0.0392 (10)	−0.0009 (6)	−0.0003 (6)	−0.0053 (7)
C2	0.0398 (10)	0.0452 (11)	0.0329 (10)	0.0068 (9)	0.0045 (8)	−0.0008 (9)
C3	0.0247 (7)	0.0247 (7)	0.0622 (18)	−0.0002 (8)	0.0055 (8)	−0.0055 (8)

Geometric parameters (Å, º)

O1—N1	1.4007 (16)	C2—H2A	0.97 (2)
O1—H1	0.99 (3)	C2—H2B	0.99 (2)
N1—C1	1.281 (2)	C2—H2C	0.97 (3)
C1—C2	1.486 (3)	C3—H3	0.98 (2)
C1—C3	1.5090 (18)
N1—O1—H1	99.1 (14)	H2A—C2—H2B	107 (2)
C1—N1—O1	112.30 (13)	C1—C2—H2C	111.2 (15)
N1—C1—C2	123.95 (13)	H2A—C2—H2C	109 (2)
N1—C1—C3	115.81 (13)	H2B—C2—H2C	104 (2)
C2—C1—C3	120.21 (13)	C1—C3—C1^i	113.00 (18)
C1—C2—H2A	112.2 (15)	C1—C3—H3	109.7 (14)
C1—C2—H2B	112.8 (14)	C1^i—C3—H3	109.3 (14)
H1—O1—N1—C1	175.6 (14)	N1—C1—C3—C1^i	119.77 (15)
O1—N1—C1—C2	−1.1 (2)	C2—C1—C3—C1^i	−62.04 (13)
O1—N1—C1—C3	177.05 (13)

Symmetry code: (i) y−1/2, x+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^ii	0.99 (3)	1.78 (3)	2.767 (2)	170 (2)

Symmetry code: (ii) −y+1, x, −z.