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The conformations of NH and CH
3 of the title compound, C
7H
11NO
2, 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.
Supporting information
CCDC reference: 620518
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
No syntax errors found
No errors found in this datablock
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
top
Crystal data top
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) Å3 | 0.51 × 0.12 × 0.11 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.1094P)2 + 0.1705P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.86 | 2.27 | 2.946 (1) | 135 |
C7—H7C···O1ii | 0.96 | 2.52 | 3.455 (3) | 165 |
C6—H6···O2iii | 0.93 | 2.68 | 3.593 (2) | 166 |
C5—H5A···O2iii | 0.96 | 2.71 | 3.353 (1) | 125 |
C5—H5B···O2iv | 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. |

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