Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044406/cv2297sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044406/cv2297Isup2.hkl |
CCDC reference: 663773
A mixture of iso-butyryl chloride (2 mmol) and hydrazine hydrate (1.00 mmol) was well stirred at room temperature for 20 minutes. The crude compound was purified by recrystallization from ethanol. Elemental analysis: calculated for C8H16N2O2: C 55.79, H 9.36, N 16.27%; found: C 55.73, H 9.42, N 16.35%.
All H atoms were placed in idealized positions (C—H 0.96–0.98 Å, N—H 0.86 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(parent atom).
In this paper,we present a title compound, 1,2-Diisobutyrylhydrazine,(I), synthesized through the substituted reaction of iso-butyryl chloride with hydrazine hydrate under mild conditions.
In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in 1,2-dibenzoylhydrazine (Shanmuga Sundara Raj et al., 2000).
In the crystal, the molecules lies on inversion centers. There exist typical intermolecular N—H···O hydrogen bonds (Table 1), which link the molecules into ribbons extended along the a axis.
For the crystal structure of 1,2-dibenzoylhydrazine, see: Shanmuga Sundara Raj et al. (2000).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C8H16N2O2 | F(000) = 188 |
Mr = 172.23 | Dx = 1.107 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7758 (8) Å | Cell parameters from 540 reflections |
b = 10.9093 (13) Å | θ = 2.8–22.2° |
c = 9.9204 (12) Å | µ = 0.08 mm−1 |
β = 91.024 (1)° | T = 298 K |
V = 516.78 (12) Å3 | Block, colourless |
Z = 2 | 0.37 × 0.18 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 914 independent reflections |
Radiation source: fine-focus sealed tube | 557 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
phi and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
Tmin = 0.971, Tmax = 0.988 | k = −12→12 |
2549 measured reflections | l = −11→8 |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1473P)2] where P = (Fo2 + 2Fc2)/3 |
914 reflections | (Δ/σ)max = 0.001 |
57 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C8H16N2O2 | V = 516.78 (12) Å3 |
Mr = 172.23 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.7758 (8) Å | µ = 0.08 mm−1 |
b = 10.9093 (13) Å | T = 298 K |
c = 9.9204 (12) Å | 0.37 × 0.18 × 0.15 mm |
β = 91.024 (1)° |
Bruker SMART CCD area-detector diffractometer | 914 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 557 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.988 | Rint = 0.065 |
2549 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.31 e Å−3 |
914 reflections | Δρmin = −0.24 e Å−3 |
57 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.5501 (5) | 0.0388 (2) | 0.9509 (2) | 0.0516 (8) | |
H1 | 0.7270 | 0.0428 | 0.9368 | 0.062* | |
O1 | 0.1184 (4) | 0.10264 (19) | 0.8985 (2) | 0.0655 (9) | |
C1 | 0.3724 (6) | 0.1075 (2) | 0.8781 (3) | 0.0465 (8) | |
C2 | 0.4985 (7) | 0.1882 (3) | 0.7727 (3) | 0.0651 (11) | |
H2 | 0.7029 | 0.1858 | 0.7827 | 0.078* | |
C3 | 0.4004 (12) | 0.3177 (4) | 0.7895 (5) | 0.1089 (17) | |
H3A | 0.2018 | 0.3217 | 0.7733 | 0.163* | |
H3B | 0.4938 | 0.3696 | 0.7264 | 0.163* | |
H3C | 0.4428 | 0.3449 | 0.8796 | 0.163* | |
C4 | 0.4179 (13) | 0.1435 (5) | 0.6365 (4) | 0.124 (2) | |
H4A | 0.4935 | 0.0630 | 0.6233 | 0.186* | |
H4B | 0.4904 | 0.1982 | 0.5699 | 0.186* | |
H4C | 0.2174 | 0.1404 | 0.6281 | 0.186* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0353 (13) | 0.0611 (17) | 0.0587 (16) | 0.0001 (11) | 0.0101 (10) | 0.0209 (12) |
O1 | 0.0347 (12) | 0.0771 (16) | 0.0851 (18) | 0.0045 (10) | 0.0088 (10) | 0.0328 (13) |
C1 | 0.0349 (15) | 0.0500 (16) | 0.0547 (17) | 0.0014 (12) | 0.0048 (12) | 0.0114 (14) |
C2 | 0.050 (2) | 0.075 (2) | 0.071 (2) | 0.0024 (16) | 0.0088 (16) | 0.0320 (19) |
C3 | 0.138 (4) | 0.075 (3) | 0.115 (3) | −0.003 (3) | 0.030 (3) | 0.036 (3) |
C4 | 0.172 (5) | 0.121 (4) | 0.080 (3) | −0.025 (4) | 0.038 (3) | 0.016 (3) |
N1—C1 | 1.335 (3) | C2—H2 | 0.9800 |
N1—N1i | 1.382 (4) | C3—H3A | 0.9600 |
N1—H1 | 0.8600 | C3—H3B | 0.9600 |
O1—C1 | 1.235 (3) | C3—H3C | 0.9600 |
C1—C2 | 1.501 (4) | C4—H4A | 0.9600 |
C2—C4 | 1.480 (5) | C4—H4B | 0.9600 |
C2—C3 | 1.499 (5) | C4—H4C | 0.9600 |
C1—N1—N1i | 120.0 (3) | C2—C3—H3A | 109.5 |
C1—N1—H1 | 120.0 | C2—C3—H3B | 109.5 |
N1i—N1—H1 | 120.0 | H3A—C3—H3B | 109.5 |
O1—C1—N1 | 120.3 (3) | C2—C3—H3C | 109.5 |
O1—C1—C2 | 123.2 (2) | H3A—C3—H3C | 109.5 |
N1—C1—C2 | 116.6 (3) | H3B—C3—H3C | 109.5 |
C4—C2—C3 | 109.6 (4) | C2—C4—H4A | 109.5 |
C4—C2—C1 | 110.0 (3) | C2—C4—H4B | 109.5 |
C3—C2—C1 | 110.2 (3) | H4A—C4—H4B | 109.5 |
C4—C2—H2 | 109.0 | C2—C4—H4C | 109.5 |
C3—C2—H2 | 109.0 | H4A—C4—H4C | 109.5 |
C1—C2—H2 | 109.0 | H4B—C4—H4C | 109.5 |
Symmetry code: (i) −x+1, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.86 | 2.02 | 2.858 (3) | 164 |
Symmetry code: (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H16N2O2 |
Mr | 172.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 4.7758 (8), 10.9093 (13), 9.9204 (12) |
β (°) | 91.024 (1) |
V (Å3) | 516.78 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.37 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.971, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2549, 914, 557 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.236, 0.99 |
No. of reflections | 914 |
No. of parameters | 57 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.02 | 2.858 (3) | 164.0 |
Symmetry code: (i) x+1, y, z. |
In this paper,we present a title compound, 1,2-Diisobutyrylhydrazine,(I), synthesized through the substituted reaction of iso-butyryl chloride with hydrazine hydrate under mild conditions.
In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in 1,2-dibenzoylhydrazine (Shanmuga Sundara Raj et al., 2000).
In the crystal, the molecules lies on inversion centers. There exist typical intermolecular N—H···O hydrogen bonds (Table 1), which link the molecules into ribbons extended along the a axis.