N′-(1-Phenyl­ethyl­idene)acetohydrazide

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.

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

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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 U_iso = 1.2(C) or 1.5U_eq(C_methyl).

Computing details

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

	Fig. 1. View of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	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

Crystal data

C10H12N2O	Z = 4
Mr = 176.22	F(000) = 376
Monoclinic, P21/c	Dx = 1.229 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.3681 (18) Å	θ = 2.2–26.3°
b = 9.361 (3) Å	µ = 0.08 mm^−1
c = 19.033 (6) Å	T = 294 K
β = 95.496 (6)°	Block, colourless
V = 952.0 (5) Å^3	0.26 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 26.3°, θmin = 2.2°
φ and ω scans	h = −6→6
5285 measured reflections	k = −9→11
1940 independent reflections	l = −23→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0397P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1940 reflections	Δρmax = 0.19 e Å^−3
125 parameters	Δρmin = −0.14 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.067 (6)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.4564 (3)	0.56158 (18)	0.58573 (8)	0.0711 (6)
N1	1.0181 (3)	0.72134 (19)	0.46283 (10)	0.0492 (5)
N2	1.2145 (4)	0.6349 (2)	0.48995 (10)	0.0527 (6)
C1	0.5972 (4)	0.8765 (2)	0.41812 (12)	0.0505 (7)
H1	0.6218	0.8495	0.4653	0.061*
C2	0.4048 (5)	0.9687 (3)	0.39673 (12)	0.0586 (7)
H2	0.3014	1.0030	0.4294	0.070*
C3	0.3650 (5)	1.0105 (3)	0.32713 (14)	0.0616 (8)
H3	0.2363	1.0736	0.3128	0.074*
C4	0.5168 (5)	0.9580 (3)	0.27914 (13)	0.0611 (7)
H4	0.4898	0.9851	0.2320	0.073*
C5	0.7111 (4)	0.8644 (2)	0.30053 (12)	0.0560 (7)
H5	0.8125	0.8294	0.2675	0.067*
C6	0.7554 (4)	0.8228 (2)	0.37083 (11)	0.0431 (6)
C7	0.9639 (4)	0.7243 (2)	0.39541 (12)	0.0463 (6)
C8	1.0931 (5)	0.6416 (2)	0.34212 (12)	0.0623 (8)
H8A	1.2002	0.7043	0.3188	0.093*
H8B	0.9704	0.6006	0.3080	0.093*
H8C	1.1915	0.5668	0.3655	0.093*
C9	1.2788 (5)	0.6354 (3)	0.56074 (13)	0.0528 (7)
C10	1.1281 (5)	0.7261 (3)	0.60558 (12)	0.0659 (8)
H10A	1.1863	0.7125	0.6544	0.099*
H10B	0.9550	0.6994	0.5979	0.099*
H10C	1.1462	0.8248	0.5932	0.099*
H2A	1.302 (4)	0.576 (2)	0.4637 (10)	0.070 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0738 (13)	0.0854 (13)	0.0519 (11)	0.0266 (11)	−0.0058 (10)	0.0042 (9)
N1	0.0445 (12)	0.0578 (12)	0.0446 (12)	−0.0008 (10)	−0.0001 (10)	0.0073 (10)
N2	0.0549 (14)	0.0599 (14)	0.0423 (13)	0.0097 (12)	−0.0002 (11)	0.0043 (11)
C1	0.0533 (16)	0.0593 (15)	0.0381 (14)	−0.0005 (13)	0.0000 (12)	0.0051 (12)
C2	0.0571 (17)	0.0710 (18)	0.0472 (16)	0.0068 (15)	0.0029 (13)	−0.0075 (13)
C3	0.0572 (18)	0.0659 (18)	0.0598 (18)	0.0079 (14)	−0.0053 (15)	0.0019 (14)
C4	0.0628 (19)	0.0726 (18)	0.0464 (16)	−0.0014 (15)	−0.0031 (15)	0.0140 (14)
C5	0.0569 (17)	0.0689 (17)	0.0421 (15)	−0.0012 (14)	0.0039 (12)	0.0026 (13)
C6	0.0434 (14)	0.0492 (15)	0.0362 (13)	−0.0071 (12)	0.0011 (11)	0.0000 (11)
C7	0.0466 (15)	0.0484 (14)	0.0433 (14)	−0.0056 (12)	0.0016 (12)	−0.0015 (12)
C8	0.0690 (18)	0.0666 (16)	0.0499 (15)	0.0078 (14)	−0.0017 (13)	−0.0038 (13)
C9	0.0566 (17)	0.0555 (16)	0.0460 (16)	−0.0005 (14)	0.0032 (13)	0.0029 (13)
C10	0.0755 (19)	0.0724 (18)	0.0489 (15)	0.0095 (15)	0.0013 (14)	−0.0001 (13)

Geometric parameters (Å, º)

O1—C9	1.235 (3)	C4—H4	0.9300
N1—C7	1.289 (2)	C5—C6	1.392 (3)
N1—N2	1.389 (2)	C5—H5	0.9300
N2—C9	1.358 (3)	C6—C7	1.490 (3)
N2—H2A	0.904 (10)	C7—C8	1.498 (3)
C1—C2	1.378 (3)	C8—H8A	0.9600
C1—C6	1.389 (3)	C8—H8B	0.9600
C1—H1	0.9300	C8—H8C	0.9600
C2—C3	1.378 (3)	C9—C10	1.496 (3)
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.372 (3)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.393 (3)
C7—N1—N2	118.3 (2)	C1—C6—C7	120.5 (2)
C9—N2—N1	118.6 (2)	C5—C6—C7	121.9 (2)
C9—N2—H2A	117.1 (14)	N1—C7—C6	114.7 (2)
N1—N2—H2A	124.3 (14)	N1—C7—C8	126.0 (2)
C2—C1—C6	121.5 (2)	C6—C7—C8	119.32 (19)
C2—C1—H1	119.2	C7—C8—H8A	109.5
C6—C1—H1	119.2	C7—C8—H8B	109.5
C1—C2—C3	120.3 (2)	H8A—C8—H8B	109.5
C1—C2—H2	119.8	C7—C8—H8C	109.5
C3—C2—H2	119.8	H8A—C8—H8C	109.5
C4—C3—C2	119.4 (2)	H8B—C8—H8C	109.5
C4—C3—H3	120.3	O1—C9—N2	119.6 (2)
C2—C3—H3	120.3	O1—C9—C10	122.5 (2)
C3—C4—C5	120.4 (2)	N2—C9—C10	117.9 (2)
C3—C4—H4	119.8	C9—C10—H10A	109.5
C5—C4—H4	119.8	C9—C10—H10B	109.5
C6—C5—C4	120.8 (2)	H10A—C10—H10B	109.5
C6—C5—H5	119.6	C9—C10—H10C	109.5
C4—C5—H5	119.6	H10A—C10—H10C	109.5
C1—C6—C5	117.6 (2)	H10B—C10—H10C	109.5
C7—N1—N2—C9	177.5 (2)	N2—N1—C7—C6	−178.45 (18)
C6—C1—C2—C3	−0.1 (3)	N2—N1—C7—C8	0.4 (3)
C1—C2—C3—C4	0.7 (3)	C1—C6—C7—N1	−15.2 (3)
C2—C3—C4—C5	−0.6 (4)	C5—C6—C7—N1	164.71 (19)
C3—C4—C5—C6	−0.2 (3)	C1—C6—C7—C8	165.8 (2)
C2—C1—C6—C5	−0.6 (3)	C5—C6—C7—C8	−14.2 (3)
C2—C1—C6—C7	179.33 (19)	N1—N2—C9—O1	−178.5 (2)
C4—C5—C6—C1	0.8 (3)	N1—N2—C9—C10	1.9 (3)
C4—C5—C6—C7	−179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.91 (2)	2.11 (2)	3.011 (3)	172 (2)
C8—H8C···N2	0.96	2.44	2.827 (3)	103
C8—H8C···O1^i	0.96	2.35	3.273 (3)	160

Symmetry code: (i) −x+3, −y+1, −z+1.