In the title structure, C
4H
10N
2O, the molecules stack with intermolecular N—H
O hydrogen bonds along the
b axis and additional intermolecular N—H
N hydrogen bonds form a network orthogonal to the
c axis.
Supporting information
CCDC reference: 640485
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.003 Å
- R factor = 0.073
- wR factor = 0.191
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
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No errors found in this datablock
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1997) and publCIF (Westrip, 2007).
2-Methylpropionohydrazide
top
Crystal data top
C4H10N2O | F(000) = 448 |
Mr = 102.08 | Dx = 1.165 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9311 reflections |
a = 11.0189 (19) Å | θ = 5.3–61.0° |
b = 4.8781 (9) Å | µ = 0.09 mm−1 |
c = 21.677 (4) Å | T = 100 K |
V = 1165.2 (4) Å3 | Plate, colourless |
Z = 8 | 0.59 × 0.46 × 0.18 mm |
Data collection top
Bruker SMART APEX CCD diffractometer | 1246 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.063 |
Graphite monochromator | θmax = 30.5°, θmin = 1.9° |
ω scans | h = −15→14 |
8412 measured reflections | k = −6→6 |
1755 independent reflections | l = −30→30 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.073 | w = 1/[σ2(Fo2) + (0.0748P)2 + 0.9877P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.191 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.44 e Å−3 |
1755 reflections | Δρmin = −0.29 e Å−3 |
104 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.34101 (18) | 0.7903 (4) | 0.48473 (8) | 0.0254 (4) | |
N2 | 0.38704 (17) | 0.8527 (3) | 0.54404 (8) | 0.0244 (4) | |
C1 | 0.42395 (19) | 0.6629 (4) | 0.58377 (10) | 0.0238 (4) | |
O1 | 0.41985 (15) | 0.4143 (3) | 0.57242 (7) | 0.0290 (4) | |
C2 | 0.4730 (2) | 0.7685 (4) | 0.64454 (10) | 0.0266 (5) | |
C3 | 0.6052 (2) | 0.6864 (6) | 0.65061 (12) | 0.0348 (6) | |
C4 | 0.3968 (2) | 0.6531 (5) | 0.69710 (11) | 0.0339 (5) | |
H1A | 0.292 (3) | 0.643 (6) | 0.4885 (12) | 0.033 (7)* | |
H1B | 0.408 (3) | 0.734 (6) | 0.4627 (13) | 0.037 (7)* | |
H2N | 0.392 (2) | 1.021 (7) | 0.5539 (12) | 0.032 (7)* | |
H2A | 0.469 (2) | 0.966 (6) | 0.6446 (10) | 0.028 (6)* | |
H3A | 0.611 (3) | 0.482 (7) | 0.6498 (13) | 0.037 (7)* | |
H3B | 0.640 (3) | 0.748 (6) | 0.6876 (13) | 0.038 (7)* | |
H3C | 0.649 (3) | 0.755 (7) | 0.6196 (15) | 0.048 (8)* | |
H4A | 0.403 (2) | 0.447 (6) | 0.6966 (12) | 0.038 (7)* | |
H4B | 0.426 (2) | 0.708 (5) | 0.7355 (12) | 0.030 (6)* | |
H4C | 0.309 (3) | 0.696 (6) | 0.6935 (13) | 0.040 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0269 (9) | 0.0188 (8) | 0.0306 (9) | −0.0019 (7) | −0.0010 (7) | −0.0016 (7) |
N2 | 0.0290 (9) | 0.0126 (8) | 0.0315 (9) | 0.0000 (7) | −0.0022 (7) | −0.0021 (6) |
C1 | 0.0244 (10) | 0.0152 (9) | 0.0317 (10) | 0.0002 (7) | 0.0015 (8) | −0.0005 (7) |
O1 | 0.0377 (9) | 0.0113 (7) | 0.0380 (8) | 0.0000 (6) | −0.0036 (6) | −0.0019 (6) |
C2 | 0.0317 (11) | 0.0166 (9) | 0.0314 (10) | −0.0011 (8) | −0.0020 (8) | −0.0005 (7) |
C3 | 0.0327 (13) | 0.0374 (14) | 0.0343 (12) | −0.0053 (10) | −0.0013 (10) | −0.0035 (10) |
C4 | 0.0362 (13) | 0.0321 (12) | 0.0333 (11) | 0.0007 (10) | 0.0036 (9) | −0.0024 (9) |
Geometric parameters (Å, º) top
N1—N2 | 1.415 (2) | N2—H2N | 0.85 (3) |
N2—C1 | 1.328 (3) | C2—H2A | 0.96 (3) |
C1—O1 | 1.238 (2) | C3—H3A | 1.00 (3) |
C1—C2 | 1.514 (3) | C3—H3B | 0.94 (3) |
C2—C3 | 1.516 (3) | C3—H3C | 0.89 (3) |
C2—C4 | 1.523 (3) | C4—H4A | 1.01 (3) |
N1—H1A | 0.90 (3) | C4—H4B | 0.93 (3) |
N1—H1B | 0.92 (3) | C4—H4C | 1.00 (3) |
| | | |
N1—N2—C1 | 123.28 (17) | H3A—C3—H3C | 109 (3) |
N2—C1—O1 | 122.9 (2) | H3B—C3—H3C | 108 (3) |
O1—C1—C2 | 121.26 (19) | C2—C4—H4A | 108.7 (16) |
N2—C1—C2 | 115.86 (18) | C2—C4—H4B | 112.0 (16) |
C1—C2—C3 | 109.18 (18) | H4A—C4—H4B | 106 (2) |
C1—C2—C4 | 109.16 (18) | C2—C4—H4C | 113.7 (16) |
C3—C2—C4 | 111.5 (2) | H4A—C4—H4C | 106 (2) |
C1—C2—H2A | 109.0 (14) | H4B—C4—H4C | 110 (2) |
C3—C2—H2A | 107.9 (16) | N2—N1—H1A | 107.7 (17) |
C4—C2—H2A | 110.0 (14) | N2—N1—H1B | 104.3 (17) |
C2—C3—H3A | 108.9 (17) | H1A—N1—H1B | 107 (2) |
C2—C3—H3B | 112.4 (18) | C1—N2—H2N | 119.3 (19) |
H3A—C3—H3B | 108 (2) | N1—N2—H2N | 117.4 (19) |
C2—C3—H3C | 111 (2) | | |
| | | |
O1—C1—C2—C3 | 62.2 (3) | N2—C1—C2—C4 | 120.4 (2) |
N2—C1—C2—C3 | −117.4 (2) | O1—C1—N2—N1 | −0.9 (3) |
O1—C1—C2—C4 | −60.0 (3) | C2—C1—N2—N1 | 178.73 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.85 (3) | 1.98 (3) | 2.831 (2) | 175 (3) |
N1—H1B···O1ii | 0.92 (3) | 2.17 (3) | 3.078 (3) | 169 (2) |
N1—H1A···N1iii | 0.90 (3) | 2.26 (3) | 3.158 (3) | 172 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y−1/2, z. |