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Acta Cryst. (2007). E63, o3375    [ doi:10.1107/S1600536807031662 ]

Acetophenone propionylhydrazone

H.-M. Guo

Abstract top

In the crystal structure of the title compound, C11H14N2O, there are two crystallographically independent molecules in the asymmetric unit, which are connected into dimers via N-H...O hydrogen bonding.

Comment top

The structure determination of the title compound (I) was undertaken as a part of our project on the synthesis of new schiff base compounds. The crystal structure of the title compound consists of two crystallographically independent molecules of similar conformation. Both molecules are are connected into dimers via N—H···O hydrogen bonding between the amino and the carbonyl group. Bond lengths and angles of these hydrogen bonds shows, that this is a strong interaction.

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Experimental top

Acetophenone (0.1 mol)and propionylhydrazine (0.1 mol)were mixed in ethanol (30 ml) and were heated under reflux for 5 h. The mixture was transfered into water to afford a colourless solid if I, which were filtered off, washed with water and dried at room temperature. Single crystals of the title compound were obtained by recrystallization from EtOH at room temperature.

Refinement top

C—H H atoms were positioned with idealized geometry and refined isotropic using a riding model with C—H distances of =0.93–0.97Å and Uiso=1.2–1.5Ueq(parent atom). The N—H H atoms were located in difference map, their bond lengths set to ideal values and afterwards they were refined using a riding model.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Acetophenone propionylhydrazone top
Crystal data top
C11H14N2OZ = 4
Mr = 190.24F(000) = 408
Triclinic, P1Dx = 1.163 Mg m−3
a = 9.554 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.007 (8) ÅCell parameters from 1128 reflections
c = 12.555 (9) Åθ = 2.3–25.7°
α = 76.603 (13)°µ = 0.08 mm−1
β = 68.836 (12)°T = 293 K
γ = 81.643 (13)°Block, colorless
V = 1086.4 (14) Å30.22 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3810 independent reflections
Radiation source: fine-focus sealed tube1798 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −11→10
Tmin = 0.983, Tmax = 0.992k = −10→11
5630 measured reflectionsl = −14→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.0791P)2 + 0.1785P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
3810 reflectionsΔρmax = 0.18 e Å−3
258 parametersΔρmin = −0.13 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (3)
Crystal data top
C11H14N2Oγ = 81.643 (13)°
Mr = 190.24V = 1086.4 (14) Å3
Triclinic, P1Z = 4
a = 9.554 (7) ÅMo Kα radiation
b = 10.007 (8) ŵ = 0.08 mm−1
c = 12.555 (9) ÅT = 293 K
α = 76.603 (13)°0.22 × 0.20 × 0.10 mm
β = 68.836 (12)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3810 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1798 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.992Rint = 0.028
5630 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.191Δρmax = 0.18 e Å−3
S = 1.01Δρmin = −0.13 e Å−3
3810 reflectionsAbsolute structure: ?
258 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

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
xyzUiso*/Ueq
O10.1027 (3)0.6056 (2)0.53651 (18)0.0901 (8)
O20.1040 (2)0.1031 (2)0.54184 (17)0.0854 (7)
N10.1903 (2)0.6784 (2)0.2353 (2)0.0581 (6)
N20.1246 (3)0.6901 (2)0.3508 (2)0.0648 (7)
H20.05860.75650.37010.078*
N30.1916 (2)0.1813 (2)0.2399 (2)0.0557 (6)
N40.1230 (3)0.1879 (2)0.3564 (2)0.0634 (7)
H40.05240.25050.37690.076*
C10.3038 (3)0.6283 (3)0.0099 (3)0.0641 (8)
H10.30300.55400.07030.077*
C20.3745 (4)0.6114 (4)−0.1036 (3)0.0765 (10)
H2A0.42000.5260−0.11900.092*
C30.3779 (4)0.7198 (4)−0.1938 (3)0.0876 (11)
H30.42520.7080−0.27040.105*
C40.3116 (4)0.8454 (4)−0.1710 (3)0.0891 (11)
H4A0.31480.9192−0.23230.107*
C50.2397 (3)0.8634 (3)−0.0571 (3)0.0715 (9)
H50.19510.9494−0.04280.086*
C60.2334 (3)0.7548 (3)0.0357 (2)0.0530 (7)
C70.1579 (3)0.7736 (3)0.1579 (2)0.0531 (7)
C80.0530 (4)0.8986 (3)0.1836 (3)0.0752 (9)
H8A−0.03130.87290.25280.113*
H8B0.01810.93650.11930.113*
H8C0.10530.96610.19500.113*
C90.1646 (3)0.5966 (3)0.4334 (3)0.0653 (8)
C100.2856 (4)0.4870 (3)0.3955 (3)0.0767 (10)
H10A0.37570.53010.34090.092*
H10B0.25350.43190.35550.092*
C110.3227 (4)0.3942 (4)0.4964 (3)0.1062 (14)
H11A0.35940.44750.53400.159*
H11B0.39840.32420.46830.159*
H11C0.23370.35180.55110.159*
C120.3670 (3)0.1940 (3)0.0065 (3)0.0661 (9)
H120.41550.16130.06070.079*
C130.4412 (4)0.1836 (4)−0.1083 (3)0.0777 (10)
H130.53870.1429−0.13050.093*
C140.3726 (4)0.2329 (4)−0.1901 (3)0.0799 (10)
H140.42340.2263−0.26750.096*
C150.2291 (4)0.2917 (3)−0.1567 (3)0.0796 (10)
H150.18220.3251−0.21180.096*
C160.1530 (3)0.3018 (3)−0.0415 (3)0.0676 (9)
H160.05530.3421−0.02010.081*
C170.2206 (3)0.2526 (3)0.0425 (2)0.0521 (7)
C180.1405 (3)0.2647 (3)0.1661 (2)0.0525 (7)
C190.0089 (4)0.3676 (3)0.1965 (3)0.0862 (11)
H19A−0.08220.32050.23310.129*
H19B0.00460.43020.12690.129*
H19C0.02000.41810.24900.129*
C200.1663 (3)0.0963 (3)0.4384 (3)0.0621 (8)
C210.2895 (3)−0.0106 (3)0.3990 (3)0.0734 (9)
H21A0.37850.03470.34510.088*
H21B0.2589−0.06500.35750.088*
C220.3283 (4)−0.1046 (4)0.4975 (3)0.1058 (14)
H22A0.3711−0.05320.53270.159*
H22B0.3999−0.17680.46850.159*
H22C0.2390−0.14380.55450.159*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1141 (19)0.0844 (16)0.0533 (14)0.0394 (13)−0.0209 (13)−0.0188 (12)
O20.1033 (17)0.0857 (16)0.0496 (14)0.0328 (13)−0.0186 (12)−0.0157 (12)
N10.0622 (15)0.0567 (15)0.0493 (15)0.0053 (12)−0.0157 (12)−0.0094 (12)
N20.0728 (17)0.0587 (16)0.0508 (15)0.0214 (13)−0.0159 (13)−0.0118 (13)
N30.0602 (15)0.0558 (15)0.0482 (15)0.0037 (12)−0.0170 (12)−0.0115 (12)
N40.0691 (16)0.0602 (16)0.0502 (15)0.0189 (13)−0.0159 (13)−0.0120 (13)
C10.070 (2)0.060 (2)0.061 (2)0.0004 (16)−0.0227 (16)−0.0115 (16)
C20.085 (2)0.078 (2)0.064 (2)0.0070 (18)−0.0194 (18)−0.0261 (19)
C30.096 (3)0.102 (3)0.056 (2)0.009 (2)−0.0174 (18)−0.022 (2)
C40.104 (3)0.094 (3)0.054 (2)0.015 (2)−0.0223 (19)−0.006 (2)
C50.077 (2)0.068 (2)0.060 (2)0.0120 (17)−0.0219 (17)−0.0083 (17)
C60.0500 (17)0.0558 (18)0.0537 (18)0.0015 (14)−0.0207 (14)−0.0097 (15)
C70.0520 (17)0.0542 (18)0.0525 (18)0.0002 (14)−0.0180 (14)−0.0114 (15)
C80.096 (2)0.062 (2)0.067 (2)0.0168 (17)−0.0329 (18)−0.0168 (17)
C90.073 (2)0.060 (2)0.052 (2)0.0120 (16)−0.0153 (17)−0.0118 (17)
C100.083 (2)0.073 (2)0.063 (2)0.0287 (18)−0.0220 (17)−0.0167 (17)
C110.114 (3)0.102 (3)0.080 (3)0.050 (2)−0.033 (2)−0.014 (2)
C120.0565 (19)0.081 (2)0.060 (2)−0.0008 (16)−0.0204 (15)−0.0116 (17)
C130.060 (2)0.101 (3)0.065 (2)−0.0006 (18)−0.0099 (17)−0.024 (2)
C140.087 (3)0.092 (3)0.055 (2)−0.009 (2)−0.0150 (19)−0.0176 (19)
C150.098 (3)0.084 (2)0.060 (2)0.003 (2)−0.037 (2)−0.0108 (18)
C160.070 (2)0.068 (2)0.063 (2)0.0074 (16)−0.0270 (17)−0.0093 (17)
C170.0544 (18)0.0485 (17)0.0514 (18)−0.0057 (14)−0.0181 (15)−0.0040 (14)
C180.0515 (17)0.0495 (17)0.0526 (18)0.0038 (14)−0.0185 (14)−0.0055 (15)
C190.082 (2)0.091 (3)0.069 (2)0.0302 (19)−0.0219 (18)−0.0112 (19)
C200.068 (2)0.0589 (19)0.051 (2)0.0122 (16)−0.0174 (16)−0.0100 (16)
C210.076 (2)0.078 (2)0.058 (2)0.0263 (18)−0.0244 (16)−0.0153 (17)
C220.110 (3)0.110 (3)0.075 (3)0.053 (2)−0.033 (2)−0.011 (2)
Geometric parameters (Å, °) top
O1—C91.233 (3)C10—H10A0.9700
O2—C201.231 (3)C10—H10B0.9700
N1—C71.285 (3)C11—H11A0.9600
N1—N21.383 (3)C11—H11B0.9600
N2—C91.352 (4)C11—H11C0.9600
N2—H20.8600C12—C131.379 (4)
N3—C181.282 (3)C12—C171.390 (4)
N3—N41.384 (3)C12—H120.9300
N4—C201.353 (3)C13—C141.373 (4)
N4—H40.8600C13—H130.9300
C1—C21.377 (4)C14—C151.366 (4)
C1—C61.395 (4)C14—H140.9300
C1—H10.9300C15—C161.385 (4)
C2—C31.369 (4)C15—H150.9300
C2—H2A0.9300C16—C171.389 (4)
C3—C41.366 (5)C16—H160.9300
C3—H30.9300C17—C181.487 (4)
C4—C51.387 (4)C18—C191.499 (4)
C4—H4A0.9300C19—H19A0.9600
C5—C61.387 (4)C19—H19B0.9600
C5—H50.9300C19—H19C0.9600
C6—C71.485 (4)C20—C211.495 (4)
C7—C81.504 (4)C21—C221.498 (4)
C8—H8A0.9600C21—H21A0.9700
C8—H8B0.9600C21—H21B0.9700
C8—H8C0.9600C22—H22A0.9600
C9—C101.497 (4)C22—H22B0.9600
C10—C111.508 (4)C22—H22C0.9600
C7—N1—N2118.3 (2)H11A—C11—H11B109.5
C9—N2—N1119.6 (2)C10—C11—H11C109.5
C9—N2—H2120.2H11A—C11—H11C109.5
N1—N2—H2120.2H11B—C11—H11C109.5
C18—N3—N4118.1 (2)C13—C12—C17121.0 (3)
C20—N4—N3120.4 (2)C13—C12—H12119.5
C20—N4—H4119.8C17—C12—H12119.5
N3—N4—H4119.8C14—C13—C12120.6 (3)
C2—C1—C6121.2 (3)C14—C13—H13119.7
C2—C1—H1119.4C12—C13—H13119.7
C6—C1—H1119.4C15—C14—C13119.4 (3)
C3—C2—C1120.3 (3)C15—C14—H14120.3
C3—C2—H2A119.8C13—C14—H14120.3
C1—C2—H2A119.8C14—C15—C16120.6 (3)
C4—C3—C2119.7 (3)C14—C15—H15119.7
C4—C3—H3120.1C16—C15—H15119.7
C2—C3—H3120.1C15—C16—C17120.8 (3)
C3—C4—C5120.4 (3)C15—C16—H16119.6
C3—C4—H4A119.8C17—C16—H16119.6
C5—C4—H4A119.8C16—C17—C12117.7 (3)
C4—C5—C6120.9 (3)C16—C17—C18121.3 (3)
C4—C5—H5119.6C12—C17—C18121.1 (3)
C6—C5—H5119.6N3—C18—C17115.1 (3)
C5—C6—C1117.4 (3)N3—C18—C19124.9 (3)
C5—C6—C7121.2 (3)C17—C18—C19120.0 (3)
C1—C6—C7121.4 (3)C18—C19—H19A109.5
N1—C7—C6115.4 (3)C18—C19—H19B109.5
N1—C7—C8124.7 (3)H19A—C19—H19B109.5
C6—C7—C8119.9 (3)C18—C19—H19C109.5
C7—C8—H8A109.5H19A—C19—H19C109.5
C7—C8—H8B109.5H19B—C19—H19C109.5
H8A—C8—H8B109.5O2—C20—N4119.7 (3)
C7—C8—H8C109.5O2—C20—C21122.3 (3)
H8A—C8—H8C109.5N4—C20—C21118.0 (3)
H8B—C8—H8C109.5C20—C21—C22112.9 (3)
O1—C9—N2119.3 (3)C20—C21—H21A109.0
O1—C9—C10122.2 (3)C22—C21—H21A109.0
N2—C9—C10118.4 (3)C20—C21—H21B109.0
C9—C10—C11112.4 (3)C22—C21—H21B109.0
C9—C10—H10A109.1H21A—C21—H21B107.8
C11—C10—H10A109.1C21—C22—H22A109.5
C9—C10—H10B109.1C21—C22—H22B109.5
C11—C10—H10B109.1H22A—C22—H22B109.5
H10A—C10—H10B107.8C21—C22—H22C109.5
C10—C11—H11A109.5H22A—C22—H22C109.5
C10—C11—H11B109.5H22B—C22—H22C109.5
C7—N1—N2—C9−175.3 (3)N2—C9—C10—C11177.6 (3)
C18—N3—N4—C20175.7 (3)C17—C12—C13—C140.9 (5)
C6—C1—C2—C30.5 (5)C12—C13—C14—C15−0.5 (5)
C1—C2—C3—C40.4 (5)C13—C14—C15—C160.0 (5)
C2—C3—C4—C5−0.6 (6)C14—C15—C16—C170.0 (5)
C3—C4—C5—C6−0.1 (5)C15—C16—C17—C120.4 (4)
C4—C5—C6—C10.9 (4)C15—C16—C17—C18179.2 (3)
C4—C5—C6—C7179.4 (3)C13—C12—C17—C16−0.8 (4)
C2—C1—C6—C5−1.2 (4)C13—C12—C17—C18−179.6 (3)
C2—C1—C6—C7−179.6 (3)N4—N3—C18—C17179.5 (2)
N2—N1—C7—C6179.6 (2)N4—N3—C18—C19−1.4 (4)
N2—N1—C7—C80.1 (4)C16—C17—C18—N3159.4 (3)
C5—C6—C7—N1−163.5 (3)C12—C17—C18—N3−21.8 (4)
C1—C6—C7—N114.9 (4)C16—C17—C18—C19−19.8 (4)
C5—C6—C7—C816.0 (4)C12—C17—C18—C19159.0 (3)
C1—C6—C7—C8−165.6 (3)N3—N4—C20—O2−179.8 (3)
N1—N2—C9—O1−178.1 (3)N3—N4—C20—C210.0 (4)
N1—N2—C9—C103.2 (4)O2—C20—C21—C22−0.8 (5)
O1—C9—C10—C11−1.1 (5)N4—C20—C21—C22179.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.112.954 (3)166
N4—H4···O1i0.862.102.937 (3)166
Symmetry codes: (i) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.112.954 (3)166
N4—H4···O1i0.862.102.937 (3)166
Symmetry codes: (i) −x, −y+1, −z+1.
references
References top

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1990). SHELXTL/PC. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. SHELXTL/PC or just SHELXTL as above?

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.