2-Methyl­propionohydrazide

In the title structure, C₄H₁₀N₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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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Computing details

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

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.59 × 0.46 × 0.18 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.073	w = 1/[σ^2(Fo^2) + (0.0748P)^2 + 0.9877P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1^i	0.85 (3)	1.98 (3)	2.831 (2)	175 (3)
N1—H1B···O1^ii	0.92 (3)	2.17 (3)	3.078 (3)	169 (2)
N1—H1A···N1^iii	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.