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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.076
- wR factor = 0.236
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the crystal structure of 1,2-dibenzoylhydrazine, see: Shanmuga Sundara Raj et al. (2000).
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. |
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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.