Hydro­gen-bonded molecular chains in (2E)-butane-2,3-dione oxime with Z' = 3

The title compound (also known as di­acetyl monoxime), C₄H₇NO₂, crystallizes with three mol­ecules in the asymmetric unit and forms continuous hydrogen-bonded molecular chains.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.181
• Data-to-parameter ratio = 19.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.20
         From the CIF: _reflns_number_total               3745
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4655
         Completeness (_total/calc)             80.45%
          Alert A: < 85% complete (theta max?)


 Alert Level B:



RINTA_01  Alert B The value of Rint is greater than 0.15
          Rint given   0.187

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.20
         From the CIF: _reflns_number_total               3745
         From the CIF: _diffrn_reflns_limit_ max hkl   15.   15.   15.
         From the CIF: _diffrn_reflns_limit_ min hkl  -14.  -16.  -16.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   16.   18.   16.
         Calculated minimum hkl  -16.  -18.  -16.
          ALERT: Expected hkl max differ from CIF values


 1 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL972 (Sheldrick, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2001).

2,3-Butanedione monoxime

Crystal data

C4H7NO2	F(000) = 648
Mr = 101.11	Dx = 1.286 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5354 (7) Å	Cell parameters from 20830 reflections
b = 12.7225 (12) Å	θ = 1.0–30.5°
c = 11.8884 (10) Å	µ = 0.10 mm^−1
β = 116.106 (3)°	T = 120 K
V = 1566.7 (2) Å^3	Block, colourless
Z = 12	0.1 × 0.1 × 0.05 mm

Data collection

Enraf-Nonius KappaCCD area-detector diffractometer	3745 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.187
Detector resolution: 10.35 pixels mm^-1	θmax = 30.2°, θmin = 3.3°
φ and ω scans	h = −14→15
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −16→15
Tmin = 0.990, Tmax = 0.995	l = −16→15
19544 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0693P)^2] where P = (Fo^2 + 2Fc^2)/3
3745 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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
O1A	0.4844 (2)	0.1259 (2)	−0.1256 (2)	0.0389 (6)
H1A	0.5439	0.1290	−0.1480	0.047*
O2A	0.4289 (2)	0.11559 (19)	0.2320 (2)	0.0375 (6)
N1A	0.5374 (3)	0.1276 (2)	0.0047 (2)	0.0309 (7)
C1A	0.3082 (3)	0.1188 (3)	−0.0316 (3)	0.0419 (9)
H11A	0.2882	0.1176	−0.1207	0.050*
H12A	0.2681	0.1806	−0.0142	0.050*
H13A	0.2745	0.0549	−0.0104	0.050*
C2A	0.4511 (3)	0.1239 (3)	0.0453 (3)	0.0291 (8)
C3A	0.5034 (3)	0.1226 (3)	0.1836 (3)	0.0321 (8)
C4A	0.6463 (3)	0.1277 (3)	0.2619 (3)	0.0399 (9)
H41A	0.6652	0.1305	0.3507	0.048*
H42A	0.6806	0.1908	0.2399	0.048*
H43A	0.6869	0.0652	0.2465	0.048*
O1B	0.1740 (2)	0.12470 (19)	0.1799 (2)	0.0429 (7)
H1B	0.2481	0.1165	0.1842	0.052*
O2B	−0.0335 (2)	0.11724 (19)	0.4285 (2)	0.0380 (6)
N1B	0.1817 (3)	0.1221 (2)	0.3001 (2)	0.0326 (7)
C1B	−0.0571 (3)	0.1310 (4)	0.1849 (3)	0.0561 (11)
H11B	−0.0876	0.0599	0.1545	0.067*
H12B	−0.1202	0.1664	0.2063	0.067*
H13B	−0.0468	0.1708	0.1193	0.067*
C2B	0.0691 (3)	0.1245 (3)	0.2981 (3)	0.0330 (8)
C3B	0.0711 (3)	0.1212 (3)	0.4227 (3)	0.0321 (8)
C4B	0.1965 (3)	0.1228 (3)	0.5375 (3)	0.0459 (10)
H41B	0.1812	0.1122	0.6114	0.055*
H42B	0.2522	0.0666	0.5327	0.055*
H43B	0.2388	0.1909	0.5438	0.055*
O1C	0.4714 (2)	0.36171 (19)	0.1546 (2)	0.0370 (6)
H1C	0.4713	0.3673	0.0842	0.044*
O2C	0.1988 (2)	0.37064 (19)	0.3370 (2)	0.0424 (6)
N1C	0.3454 (2)	0.3717 (2)	0.1411 (2)	0.0298 (7)
C1C	0.4509 (4)	0.3447 (3)	0.3707 (3)	0.0475 (11)
H11C	0.5277	0.3266	0.3595	0.057*
H12C	0.4678	0.4085	0.4217	0.057*
H13C	0.4301	0.2867	0.4131	0.057*
C2C	0.3406 (3)	0.3632 (3)	0.2467 (3)	0.0305 (8)
C3C	0.2094 (3)	0.3763 (3)	0.2389 (3)	0.0323 (8)
C4C	0.0983 (3)	0.3977 (3)	0.1164 (3)	0.0447 (10)
H41C	0.1053	0.4693	0.0895	0.054*
H42C	0.0986	0.3474	0.0541	0.054*
H43C	0.0177	0.3908	0.1245	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0493 (15)	0.0452 (15)	0.0353 (14)	0.0006 (13)	0.0306 (12)	0.0008 (13)
O2A	0.0433 (15)	0.0400 (15)	0.0427 (14)	0.0002 (12)	0.0315 (13)	0.0025 (13)
N1A	0.0426 (17)	0.0305 (16)	0.0304 (17)	−0.0014 (14)	0.0258 (15)	0.0018 (14)
C1A	0.036 (2)	0.052 (2)	0.042 (2)	−0.002 (2)	0.0221 (19)	−0.004 (2)
C2A	0.0342 (19)	0.0297 (18)	0.033 (2)	−0.0005 (17)	0.0234 (17)	−0.0015 (16)
C3A	0.037 (2)	0.0252 (19)	0.043 (2)	0.0034 (16)	0.0257 (18)	0.0008 (17)
C4A	0.035 (2)	0.052 (2)	0.037 (2)	0.0006 (19)	0.0195 (17)	−0.0018 (19)
O1B	0.0459 (15)	0.0568 (16)	0.0433 (16)	0.0014 (14)	0.0354 (13)	0.0035 (14)
O2B	0.0450 (15)	0.0409 (15)	0.0465 (15)	−0.0004 (13)	0.0368 (13)	0.0010 (13)
N1B	0.0420 (19)	0.0305 (16)	0.0385 (18)	−0.0009 (15)	0.0298 (15)	0.0007 (14)
C1B	0.037 (2)	0.097 (3)	0.040 (2)	0.001 (2)	0.022 (2)	0.004 (2)
C2B	0.042 (2)	0.0307 (19)	0.039 (2)	−0.0018 (17)	0.0299 (18)	−0.0016 (18)
C3B	0.046 (2)	0.0183 (18)	0.042 (2)	−0.0006 (16)	0.0275 (19)	−0.0009 (17)
C4B	0.044 (2)	0.062 (3)	0.039 (2)	0.007 (2)	0.026 (2)	0.001 (2)
O1C	0.0380 (14)	0.0470 (16)	0.0403 (14)	0.0005 (12)	0.0303 (12)	−0.0013 (12)
O2C	0.0582 (16)	0.0392 (15)	0.0508 (16)	0.0028 (13)	0.0434 (14)	0.0018 (14)
N1C	0.0361 (17)	0.0324 (16)	0.0323 (16)	0.0028 (14)	0.0253 (14)	−0.0002 (14)
C1C	0.045 (2)	0.073 (3)	0.030 (2)	0.006 (2)	0.021 (2)	−0.0024 (19)
C2C	0.038 (2)	0.031 (2)	0.030 (2)	0.0003 (17)	0.0216 (17)	−0.0007 (16)
C3C	0.038 (2)	0.0237 (18)	0.046 (2)	0.0006 (18)	0.029 (2)	0.0007 (17)
C4C	0.034 (2)	0.055 (3)	0.051 (3)	0.0011 (18)	0.023 (2)	−0.0049 (19)

Geometric parameters (Å, º)

O1A—N1A	1.392 (3)	C1B—H13B	0.980
O1A—H1A	0.840	C2B—C3B	1.472 (4)
O2A—C3A	1.230 (3)	C3B—C4B	1.490 (5)
N1A—C2A	1.284 (4)	C4B—H41B	0.980
C1A—C2A	1.494 (5)	C4B—H42B	0.980
C1A—H11A	0.980	C4B—H43B	0.980
C1A—H12A	0.980	O1C—N1C	1.396 (3)
C1A—H13A	0.980	O1C—H1C	0.840
C2A—C3A	1.481 (5)	O2C—C3C	1.226 (4)
C3A—C4A	1.496 (5)	N1C—C2C	1.285 (4)
C4A—H41A	0.980	C1C—C2C	1.482 (5)
C4A—H42A	0.980	C1C—H11C	0.980
C4A—H43A	0.980	C1C—H12C	0.980
O1B—N1B	1.393 (3)	C1C—H13C	0.980
O1B—H1B	0.840	C2C—C3C	1.485 (4)
O2B—C3B	1.239 (4)	C3C—C4C	1.482 (5)
N1B—C2B	1.289 (4)	C4C—H41C	0.980
C1B—C2B	1.488 (5)	C4C—H42C	0.980
C1B—H11B	0.980	C4C—H43C	0.980
C1B—H12B	0.980
N1A—O1A—H1A	109.4	C3B—C2B—C1B	119.2 (3)
C2A—N1A—O1A	112.6 (3)	O2B—C3B—C2B	118.2 (3)
C2A—C1A—H11A	109.5	O2B—C3B—C4B	121.8 (3)
C2A—C1A—H12A	109.4	C2B—C3B—C4B	120.0 (3)
H11A—C1A—H12A	109.5	C3B—C4B—H41B	109.5
C2A—C1A—H13A	109.5	C3B—C4B—H42B	109.5
H11A—C1A—H13A	109.5	H41B—C4B—H42B	109.5
H12A—C1A—H13A	109.5	C3B—C4B—H43B	109.4
N1A—C2A—C3A	114.4 (3)	H41B—C4B—H43B	109.5
N1A—C2A—C1A	126.9 (3)	H42B—C4B—H43B	109.5
C3A—C2A—C1A	118.7 (3)	N1C—O1C—H1C	109.4
O2A—C3A—C2A	119.5 (3)	C2C—N1C—O1C	111.7 (2)
O2A—C3A—C4A	121.1 (3)	C2C—C1C—H11C	109.4
C2A—C3A—C4A	119.3 (3)	C2C—C1C—H12C	109.5
C3A—C4A—H41A	109.5	H11C—C1C—H12C	109.5
C3A—C4A—H42A	109.4	C2C—C1C—H13C	109.5
H41A—C4A—H42A	109.5	H11C—C1C—H13C	109.5
C3A—C4A—H43A	109.5	H12C—C1C—H13C	109.5
H41A—C4A—H43A	109.5	N1C—C2C—C1C	126.8 (3)
H42A—C4A—H43A	109.5	N1C—C2C—C3C	114.2 (3)
N1B—O1B—H1B	109.4	C1C—C2C—C3C	119.0 (3)
C2B—N1B—O1B	111.8 (3)	O2C—C3C—C4C	122.7 (3)
C2B—C1B—H11B	109.4	O2C—C3C—C2C	117.3 (3)
C2B—C1B—H12B	109.5	C4C—C3C—C2C	119.9 (3)
H11B—C1B—H12B	109.5	C3C—C4C—H41C	109.4
C2B—C1B—H13B	109.5	C3C—C4C—H42C	109.5
H11B—C1B—H13B	109.5	H41C—C4C—H42C	109.5
H12B—C1B—H13B	109.5	C3C—C4C—H43C	109.5
N1B—C2B—C3B	114.3 (3)	H41C—C4C—H43C	109.5
N1B—C2B—C1B	126.5 (3)	H42C—C4C—H43C	109.5
O1A—N1A—C2A—C3A	178.4 (3)	C1B—C2B—C3B—O2B	4.5 (5)
O1A—N1A—C2A—C1A	−0.3 (5)	N1B—C2B—C3B—C4B	4.1 (5)
N1A—C2A—C3A—O2A	−177.6 (3)	C1B—C2B—C3B—C4B	−175.4 (4)
C1A—C2A—C3A—O2A	1.2 (5)	O1C—N1C—C2C—C1C	−0.2 (5)
N1A—C2A—C3A—C4A	1.3 (4)	O1C—N1C—C2C—C3C	178.3 (3)
C1A—C2A—C3A—C4A	−180.0 (3)	N1C—C2C—C3C—O2C	−178.9 (3)
O1B—N1B—C2B—C3B	179.6 (3)	C1C—C2C—C3C—O2C	−0.3 (5)
O1B—N1B—C2B—C1B	−1.0 (5)	N1C—C2C—C3C—C4C	−0.3 (4)
N1B—C2B—C3B—O2B	−176.0 (3)	C1C—C2C—C3C—C4C	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O2A	0.84	1.90	2.727 (4)	166
O1A—H1A···O2C^i	0.84	1.87	2.699 (4)	168
O1C—H1C···O2B^i	0.84	1.84	2.677 (5)	178

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