3-(Amino­methyl­ene)pentane-2,4-dione

The orientations of NH₂ and CH₃ of the title compound, C₆H₉NO₂, are mainly stabilized by N—H...O and C—H...O intra­molecular hydrogen bonds, as well as inter­molecular N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.102
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5     ..  O1      ..      93.32 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5     ..  O1      ..      94.43 Deg.

   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
   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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

3-(Aminomethylene)pentane-2,4-dione

Crystal data

C6H9NO2	F(000) = 544
Mr = 127.14	Dx = 1.278 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C_2yc	Cell parameters from 2353 reflections
a = 6.924 (2) Å	θ = 2.5–27.4°
b = 13.396 (2) Å	µ = 0.10 mm^−1
c = 14.630 (1) Å	T = 100 K
β = 103.03 (1)°	Block, colourless
V = 1322.0 (4) Å^3	0.55 × 0.16 × 0.04 mm
Z = 8

Data collection

Oxford Diffraction GEMINI R diffractometer	1537 independent reflections
Radiation source: fine-focus sealed tube	1027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 29.0°, θmin = 3.4°
Absorption correction: analytical (Clark & Reid, 1995)	h = −9→9
Tmin = 0.898, Tmax = 1.000	k = −18→14
6668 measured reflections	l = −15→19

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)] = 0.037	Hydrogen site location: difmap for Me, geom
wR(F^2) = 0.102	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0614P)^2] where P = (Fo^2 + 2Fc^2)/3
1537 reflections	(Δ/σ)max < 0.001
88 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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
C2	0.28885 (16)	0.12452 (9)	0.80387 (8)	0.0281 (3)
C3	0.22650 (16)	0.07805 (8)	0.71200 (8)	0.0235 (3)
C6	0.22209 (16)	−0.02618 (8)	0.70813 (8)	0.0246 (3)
H6	0.2640	−0.0591	0.7651	0.030*
C4	0.16669 (16)	0.13498 (9)	0.62482 (8)	0.0258 (3)
N1	0.16639 (14)	−0.08293 (7)	0.63441 (6)	0.0290 (3)
H2B	0.1262	−0.0564	0.5799	0.035*
H2A	0.1699	−0.1468	0.6403	0.035*
C1	0.3453 (2)	0.06112 (10)	0.89126 (9)	0.0347 (3)
H1B	0.3793	0.1036	0.9454	0.042*
H1A	0.4570	0.0201	0.8877	0.042*
H1C	0.2354	0.0194	0.8963	0.042*
C5	0.1672 (2)	0.24735 (9)	0.62331 (9)	0.0352 (3)
H5C	0.1255	0.2703	0.5597	0.042*
H5B	0.2987	0.2713	0.6497	0.042*
H5A	0.0779	0.2721	0.6595	0.042*
O1	0.29708 (13)	0.21590 (6)	0.81380 (6)	0.0421 (3)
O2	0.11376 (13)	0.09082 (6)	0.54917 (5)	0.0332 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0220 (6)	0.0274 (6)	0.0365 (7)	−0.0027 (5)	0.0098 (5)	−0.0052 (5)
C3	0.0208 (6)	0.0203 (6)	0.0299 (6)	−0.0009 (5)	0.0063 (5)	−0.0017 (5)
C6	0.0213 (6)	0.0220 (6)	0.0300 (6)	0.0003 (5)	0.0044 (5)	0.0030 (5)
C4	0.0208 (6)	0.0211 (6)	0.0356 (7)	−0.0003 (5)	0.0065 (5)	−0.0003 (5)
N1	0.0351 (6)	0.0172 (5)	0.0319 (6)	−0.0001 (4)	0.0013 (4)	0.0002 (4)
C1	0.0356 (7)	0.0390 (7)	0.0298 (7)	−0.0047 (6)	0.0081 (5)	−0.0048 (5)
C5	0.0415 (8)	0.0214 (6)	0.0424 (8)	0.0001 (5)	0.0089 (6)	0.0036 (5)
O1	0.0525 (6)	0.0266 (5)	0.0459 (6)	−0.0036 (4)	0.0083 (5)	−0.0133 (4)
O2	0.0399 (5)	0.0245 (4)	0.0309 (5)	−0.0021 (4)	−0.0010 (4)	0.0016 (4)

Geometric parameters (Å, º)

C2—O1	1.2325 (14)	N1—H2B	0.8600
C2—C3	1.4556 (15)	N1—H2A	0.8600
C2—C1	1.5110 (17)	C1—H1B	0.9600
C3—C6	1.3974 (15)	C1—H1A	0.9600
C3—C4	1.4635 (16)	C1—H1C	0.9600
C6—N1	1.3048 (14)	C5—H5C	0.9600
C6—H6	0.9300	C5—H5B	0.9600
C4—O2	1.2355 (13)	C5—H5A	0.9600
C4—C5	1.5055 (15)
O1—C2—C3	121.99 (11)	H2B—N1—H2A	120.0
O1—C2—C1	117.54 (10)	C2—C1—H1B	109.5
C3—C2—C1	120.47 (11)	C2—C1—H1A	109.5
C6—C3—C2	117.64 (10)	H1B—C1—H1A	109.5
C6—C3—C4	119.08 (10)	C2—C1—H1C	109.5
C2—C3—C4	123.27 (10)	H1B—C1—H1C	109.5
N1—C6—C3	127.97 (10)	H1A—C1—H1C	109.5
N1—C6—H6	116.0	C4—C5—H5C	109.5
C3—C6—H6	116.0	C4—C5—H5B	109.5
O2—C4—C3	119.98 (10)	H5C—C5—H5B	109.5
O2—C4—C5	117.82 (10)	C4—C5—H5A	109.5
C3—C4—C5	122.19 (10)	H5C—C5—H5A	109.5
C6—N1—H2B	120.0	H5B—C5—H5A	109.5
C6—N1—H2A	120.0
O1—C2—C3—C6	180.00 (10)	C4—C3—C6—N1	−1.30 (19)
C1—C2—C3—C6	−0.30 (16)	C6—C3—C4—O2	−0.19 (17)
O1—C2—C3—C4	−0.77 (18)	C2—C3—C4—O2	−179.40 (11)
C1—C2—C3—C4	178.92 (12)	C6—C3—C4—C5	179.92 (11)
C2—C3—C6—N1	177.95 (11)	C2—C3—C4—C5	0.71 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2B···O2	0.86	2.02	2.627 (2)	127
C5—H5A···O1	0.96	2.53	2.761 (1)	93
C5—H5B···O1	0.96	2.52	2.761 (1)	94
N1—H2A···O1^i	0.86	1.95	2.795 (1)	166
N1—H2B···O2^ii	0.86	2.26	2.939 (1)	136

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x, −y, −z+1.