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

The conformations of NH and CH₃ of the title compound, C₇H₁₁NO₂, are mainly stabilized by intra­molecular N—H...O and C—H...O hydrogen bonds of 1.983, 2.579 and 2.485 Å, as well as inter­molecular N—H...O and C—H...O hydrogen bonds of 2.274, 2.520, 2.484, 2.713 and 2.683 Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.061
• wR factor = 0.165
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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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: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

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

Crystal data

C7H11NO2	F(000) = 304
Mr = 141.17	Dx = 1.252 Mg m^−3
Monoclinic, P_21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 12720 reflections
a = 3.9640 (3) Å	θ = 3.7–37.4°
b = 20.3808 (9) Å	µ = 0.09 mm^−1
c = 9.4566 (6) Å	T = 100 K
β = 101.453 (6)°	Block, colorless
V = 748.78 (8) Å^3	0.51 × 0.12 × 0.11 mm
Z = 4

Data collection

Oxford Diffraction GEMINI R diffractometer	1359 independent reflections
Radiation source: fine-focus sealed tube	1206 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 4.6°
Absorption correction: analytical (Clark & Reid, 1995)	h = −4→4
Tmin = 0.652, Tmax = 0.719	k = −24→24
15570 measured reflections	l = −11→11

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.1094P)^2 + 0.1705P] where P = (Fo^2 + 2Fc^2)/3
1359 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.29 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
C1	0.3171 (4)	0.39839 (8)	0.84863 (17)	0.0309 (4)
H1C	0.4096	0.4408	0.8792	0.037*
H1B	0.5022	0.3678	0.8504	0.037*
H1A	0.1730	0.3835	0.9126	0.037*
C2	0.1079 (4)	0.40315 (7)	0.69768 (16)	0.0260 (4)
C3	−0.0710 (4)	0.34687 (7)	0.62364 (16)	0.0239 (4)
C4	−0.0402 (4)	0.28065 (7)	0.68409 (16)	0.0246 (4)
C5	−0.2319 (4)	0.22506 (7)	0.59810 (16)	0.0272 (4)
H5C	−0.2005	0.1856	0.6546	0.033*
H5B	−0.1446	0.2187	0.5114	0.033*
H5A	−0.4726	0.2355	0.5736	0.033*
C6	−0.2878 (4)	0.35569 (7)	0.48822 (16)	0.0240 (4)
H6	−0.4031	0.3187	0.4459	0.029*
C7	−0.5782 (4)	0.41648 (8)	0.27774 (17)	0.0288 (4)
H7C	−0.7512	0.4486	0.2848	0.035*
H7B	−0.6859	0.3749	0.2513	0.035*
H7A	−0.4527	0.4299	0.2056	0.035*
O1	0.0890 (3)	0.45783 (5)	0.63815 (12)	0.0322 (4)
O2	0.1421 (3)	0.26740 (5)	0.80239 (11)	0.0317 (4)
N	−0.3441 (3)	0.41055 (6)	0.41549 (14)	0.0263 (4)
H2	−0.2357	0.4451	0.4517	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0360 (9)	0.0243 (8)	0.0300 (9)	−0.0045 (6)	0.0006 (7)	−0.0009 (6)
C2	0.0277 (8)	0.0228 (8)	0.0282 (8)	0.0005 (6)	0.0077 (6)	−0.0005 (6)
C3	0.0268 (8)	0.0205 (8)	0.0250 (8)	0.0012 (5)	0.0062 (6)	−0.0004 (6)
C4	0.0256 (8)	0.0234 (8)	0.0259 (8)	0.0008 (6)	0.0075 (6)	−0.0006 (6)
C5	0.0313 (8)	0.0202 (8)	0.0298 (8)	−0.0003 (6)	0.0053 (6)	0.0024 (6)
C6	0.0262 (8)	0.0195 (8)	0.0270 (8)	−0.0001 (5)	0.0071 (6)	−0.0011 (6)
C7	0.0320 (9)	0.0227 (8)	0.0296 (8)	0.0019 (6)	0.0013 (6)	0.0011 (6)
O1	0.0421 (7)	0.0196 (6)	0.0324 (7)	−0.0030 (4)	0.0012 (5)	0.0018 (4)
O2	0.0402 (7)	0.0256 (7)	0.0269 (7)	0.0007 (4)	0.0009 (5)	0.0036 (4)
N	0.0310 (7)	0.0194 (7)	0.0271 (7)	−0.0009 (5)	0.0023 (6)	−0.0010 (5)

Geometric parameters (Å, º)

C1—C2	1.505 (2)	C5—H5C	0.9600
C1—H1C	0.9600	C5—H5B	0.9600
C1—H1B	0.9600	C5—H5A	0.9600
C1—H1A	0.9600	C6—N	1.3085 (19)
C2—O1	1.2441 (19)	C6—H6	0.9300
C2—C3	1.453 (2)	C7—N	1.447 (2)
C3—C6	1.405 (2)	C7—H7C	0.9600
C3—C4	1.461 (2)	C7—H7B	0.9600
C4—O2	1.2352 (18)	C7—H7A	0.9600
C4—C5	1.509 (2)	N—H2	0.8600
C2—C1—H1C	109.5	H5C—C5—H5B	109.5
C2—C1—H1B	109.5	C4—C5—H5A	109.5
H1C—C1—H1B	109.5	H5C—C5—H5A	109.5
C2—C1—H1A	109.5	H5B—C5—H5A	109.5
H1C—C1—H1A	109.5	N—C6—C3	126.75 (14)
H1B—C1—H1A	109.5	N—C6—H6	116.6
O1—C2—C3	120.62 (14)	C3—C6—H6	116.6
O1—C2—C1	117.35 (13)	N—C7—H7C	109.5
C3—C2—C1	122.03 (13)	N—C7—H7B	109.5
C6—C3—C2	119.32 (13)	H7C—C7—H7B	109.5
C6—C3—C4	117.60 (13)	N—C7—H7A	109.5
C2—C3—C4	123.07 (13)	H7C—C7—H7A	109.5
O2—C4—C3	123.01 (14)	H7B—C7—H7A	109.5
O2—C4—C5	117.73 (13)	C6—N—C7	123.84 (13)
C3—C4—C5	119.25 (13)	C6—N—H2	118.1
C4—C5—H5C	109.5	C7—N—H2	118.1
C4—C5—H5B	109.5
O1—C2—C3—C6	−4.9 (2)	C6—C3—C4—C5	1.6 (2)
C1—C2—C3—C6	174.14 (13)	C2—C3—C4—C5	−179.08 (14)
O1—C2—C3—C4	175.82 (13)	C2—C3—C6—N	2.0 (2)
C1—C2—C3—C4	−5.2 (2)	C4—C3—C6—N	−178.68 (14)
C6—C3—C4—O2	−179.77 (13)	C3—C6—N—C7	−178.37 (13)
C2—C3—C4—O2	−0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H2···O1	0.86	1.98	2.622 (1)	130
C1—H1A···O2	0.96	2.58	2.771 (1)	91
C1—H1B···O2	0.96	2.49	2.771 (1)	97
N—H2···O1^i	0.86	2.27	2.946 (1)	135
C7—H7C···O1^ii	0.96	2.52	3.455 (3)	165
C6—H6···O2^iii	0.93	2.68	3.593 (2)	166
C5—H5A···O2^iii	0.96	2.71	3.353 (1)	125
C5—H5B···O2^iv	0.96	2.48	3.419 (3)	165

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