Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C10H12N2O, was prepared by the reaction between hypnone and acetohydrazide. Mol­ecules form centrosymmetric dimers through N—H...O and weak C—H...O hydrogen bonds. Weak inter­actions between the dimers and intra­molecular C—H...N hydrogen-bond inter­actions stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026748/at2312sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026748/at2312Isup2.hkl
Contains datablock I

CCDC reference: 654889

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.117
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H8C .. 1.91 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our search for new schiff base compounds we synthesized the title compound (I), and we report its structure here.

The molecules are linked together to form two dimer by N21—H2A···O1i and weak C—H···Oi hydrogen bonds [symmetry code: (i) - x + 3, - y + 1, - z + 1] (Table 2 and Fig. 2). The structure is stabilized by weak-interactions between the dimers and intarmolecular C8—H8C···N2 hydrogen bonding interactions.

Related literature top

For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

Experimental top

A mixture of the hypnone (0.1 mol), and acetohydrazide (0.1 mol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (0.087 mol, yield 87%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

The H atom bound to the N2 atom were found from a difference Fourier map and refined freely. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93–0.96 Å, and with Uiso = 1.2(C) or 1.5Ueq(Cmethyl).

Structure description top

As part of our search for new schiff base compounds we synthesized the title compound (I), and we report its structure here.

The molecules are linked together to form two dimer by N21—H2A···O1i and weak C—H···Oi hydrogen bonds [symmetry code: (i) - x + 3, - y + 1, - z + 1] (Table 2 and Fig. 2). The structure is stabilized by weak-interactions between the dimers and intarmolecular C8—H8C···N2 hydrogen bonding interactions.

For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view of the N—H.·O and weak C—H.·O hydrogen-bonded dimer. [Symmetry code: (a) - x + 3, - y + 1, - z + 1].
N'-(1-Phenylethylidene)acetohydrazide top
Crystal data top
C10H12N2OZ = 4
Mr = 176.22F(000) = 376
Monoclinic, P21/cDx = 1.229 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.3681 (18) Åθ = 2.2–26.3°
b = 9.361 (3) ŵ = 0.08 mm1
c = 19.033 (6) ÅT = 294 K
β = 95.496 (6)°Block, colourless
V = 952.0 (5) Å30.26 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
Graphite monochromatorθmax = 26.3°, θmin = 2.2°
φ and ω scansh = 66
5285 measured reflectionsk = 911
1940 independent reflectionsl = 2319
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)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0397P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1940 reflectionsΔρmax = 0.19 e Å3
125 parametersΔρmin = 0.14 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.067 (6)
Crystal data top
C10H12N2OV = 952.0 (5) Å3
Mr = 176.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.3681 (18) ŵ = 0.08 mm1
b = 9.361 (3) ÅT = 294 K
c = 19.033 (6) Å0.26 × 0.10 × 0.10 mm
β = 95.496 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
882 reflections with I > 2σ(I)
5285 measured reflectionsRint = 0.070
1940 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.19 e Å3
1940 reflectionsΔρmin = 0.14 e Å3
125 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.

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
O11.4564 (3)0.56158 (18)0.58573 (8)0.0711 (6)
N11.0181 (3)0.72134 (19)0.46283 (10)0.0492 (5)
N21.2145 (4)0.6349 (2)0.48995 (10)0.0527 (6)
C10.5972 (4)0.8765 (2)0.41812 (12)0.0505 (7)
H10.62180.84950.46530.061*
C20.4048 (5)0.9687 (3)0.39673 (12)0.0586 (7)
H20.30141.00300.42940.070*
C30.3650 (5)1.0105 (3)0.32713 (14)0.0616 (8)
H30.23631.07360.31280.074*
C40.5168 (5)0.9580 (3)0.27914 (13)0.0611 (7)
H40.48980.98510.23200.073*
C50.7111 (4)0.8644 (2)0.30053 (12)0.0560 (7)
H50.81250.82940.26750.067*
C60.7554 (4)0.8228 (2)0.37083 (11)0.0431 (6)
C70.9639 (4)0.7243 (2)0.39541 (12)0.0463 (6)
C81.0931 (5)0.6416 (2)0.34212 (12)0.0623 (8)
H8A1.20020.70430.31880.093*
H8B0.97040.60060.30800.093*
H8C1.19150.56680.36550.093*
C91.2788 (5)0.6354 (3)0.56074 (13)0.0528 (7)
C101.1281 (5)0.7261 (3)0.60558 (12)0.0659 (8)
H10A1.18630.71250.65440.099*
H10B0.95500.69940.59790.099*
H10C1.14620.82480.59320.099*
H2A1.302 (4)0.576 (2)0.4637 (10)0.070 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0738 (13)0.0854 (13)0.0519 (11)0.0266 (11)0.0058 (10)0.0042 (9)
N10.0445 (12)0.0578 (12)0.0446 (12)0.0008 (10)0.0001 (10)0.0073 (10)
N20.0549 (14)0.0599 (14)0.0423 (13)0.0097 (12)0.0002 (11)0.0043 (11)
C10.0533 (16)0.0593 (15)0.0381 (14)0.0005 (13)0.0000 (12)0.0051 (12)
C20.0571 (17)0.0710 (18)0.0472 (16)0.0068 (15)0.0029 (13)0.0075 (13)
C30.0572 (18)0.0659 (18)0.0598 (18)0.0079 (14)0.0053 (15)0.0019 (14)
C40.0628 (19)0.0726 (18)0.0464 (16)0.0014 (15)0.0031 (15)0.0140 (14)
C50.0569 (17)0.0689 (17)0.0421 (15)0.0012 (14)0.0039 (12)0.0026 (13)
C60.0434 (14)0.0492 (15)0.0362 (13)0.0071 (12)0.0011 (11)0.0000 (11)
C70.0466 (15)0.0484 (14)0.0433 (14)0.0056 (12)0.0016 (12)0.0015 (12)
C80.0690 (18)0.0666 (16)0.0499 (15)0.0078 (14)0.0017 (13)0.0038 (13)
C90.0566 (17)0.0555 (16)0.0460 (16)0.0005 (14)0.0032 (13)0.0029 (13)
C100.0755 (19)0.0724 (18)0.0489 (15)0.0095 (15)0.0013 (14)0.0001 (13)
Geometric parameters (Å, º) top
O1—C91.235 (3)C4—H40.9300
N1—C71.289 (2)C5—C61.392 (3)
N1—N21.389 (2)C5—H50.9300
N2—C91.358 (3)C6—C71.490 (3)
N2—H2A0.904 (10)C7—C81.498 (3)
C1—C21.378 (3)C8—H8A0.9600
C1—C61.389 (3)C8—H8B0.9600
C1—H10.9300C8—H8C0.9600
C2—C31.378 (3)C9—C101.496 (3)
C2—H20.9300C10—H10A0.9600
C3—C41.372 (3)C10—H10B0.9600
C3—H30.9300C10—H10C0.9600
C4—C51.393 (3)
C7—N1—N2118.3 (2)C1—C6—C7120.5 (2)
C9—N2—N1118.6 (2)C5—C6—C7121.9 (2)
C9—N2—H2A117.1 (14)N1—C7—C6114.7 (2)
N1—N2—H2A124.3 (14)N1—C7—C8126.0 (2)
C2—C1—C6121.5 (2)C6—C7—C8119.32 (19)
C2—C1—H1119.2C7—C8—H8A109.5
C6—C1—H1119.2C7—C8—H8B109.5
C1—C2—C3120.3 (2)H8A—C8—H8B109.5
C1—C2—H2119.8C7—C8—H8C109.5
C3—C2—H2119.8H8A—C8—H8C109.5
C4—C3—C2119.4 (2)H8B—C8—H8C109.5
C4—C3—H3120.3O1—C9—N2119.6 (2)
C2—C3—H3120.3O1—C9—C10122.5 (2)
C3—C4—C5120.4 (2)N2—C9—C10117.9 (2)
C3—C4—H4119.8C9—C10—H10A109.5
C5—C4—H4119.8C9—C10—H10B109.5
C6—C5—C4120.8 (2)H10A—C10—H10B109.5
C6—C5—H5119.6C9—C10—H10C109.5
C4—C5—H5119.6H10A—C10—H10C109.5
C1—C6—C5117.6 (2)H10B—C10—H10C109.5
C7—N1—N2—C9177.5 (2)N2—N1—C7—C6178.45 (18)
C6—C1—C2—C30.1 (3)N2—N1—C7—C80.4 (3)
C1—C2—C3—C40.7 (3)C1—C6—C7—N115.2 (3)
C2—C3—C4—C50.6 (4)C5—C6—C7—N1164.71 (19)
C3—C4—C5—C60.2 (3)C1—C6—C7—C8165.8 (2)
C2—C1—C6—C50.6 (3)C5—C6—C7—C814.2 (3)
C2—C1—C6—C7179.33 (19)N1—N2—C9—O1178.5 (2)
C4—C5—C6—C10.8 (3)N1—N2—C9—C101.9 (3)
C4—C5—C6—C7179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.91 (2)2.11 (2)3.011 (3)172 (2)
C8—H8C···N20.962.442.827 (3)103
C8—H8C···O1i0.962.353.273 (3)160
Symmetry code: (i) x+3, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC10H12N2O
Mr176.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)5.3681 (18), 9.361 (3), 19.033 (6)
β (°) 95.496 (6)
V3)952.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5285, 1940, 882
Rint0.070
(sin θ/λ)max1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.117, 1.03
No. of reflections1940
No. of parameters125
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.14

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.91 (2)2.11 (2)3.011 (3)172.2 (18)
C8—H8C···N20.962.442.827 (3)103
C8—H8C···O1i0.962.353.273 (3)160
Symmetry code: (i) x+3, y+1, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds