N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]acetohydrazide

The title compound, C₁₀H₁₂N₂O₂, was prepared by the reaction of o-hydroxy­hypnone and acetohydrazide. In the structure, there are intra­molecular C—H...N and O—H...N, and inter­molecular N—H...O and C—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.127
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2A    ..  H11C    ..       1.96 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
   2 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
   1 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 describe its structure here.

All of the bond lengths and angles in (I) (Fig. 1) are in normal ranges. The molecular and crystal structure is stabilized by the intramolecular C—H···N and O—H···N, and intermolecular N—H···O and C—H···O hydrogen bonding interactions.

Related literature

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

S2. Experimental

A mixture of the o-hydroxyhypnone (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 was found from a difference Fourier map and refined freely. The remained H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 - 0.96 Å and O—H = 0.82 Å and with U_iso=1.2U_eq(C) or 1.5U_eq(C_methyl, O_hydroxyl).

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. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-[1-(2-Hydroxyphenyl)ethylidene]acetohydrazide

Crystal data

C10H12N2O2	Z = 4
Mr = 192.22	F(000) = 408
Monoclinic, P21/c	Dx = 1.328 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.547 (2) Å	θ = 2.6–26.4°
b = 13.586 (4) Å	µ = 0.09 mm^−1
c = 9.642 (3) Å	T = 294 K
β = 103.427 (5)°	Block, colourless
V = 961.7 (5) Å^3	0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1423 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 26.4°, θmin = 2.6°
φ and ω scans	h = −9→9
5410 measured reflections	k = −10→16
1954 independent reflections	l = −12→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0703P)^2 + 0.1565P] where P = (Fo^2 + 2Fc^2)/3
1954 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

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
N1	0.67833 (17)	0.88541 (10)	0.06106 (13)	0.0357 (3)
C2	0.7178 (2)	0.96368 (11)	−0.00015 (15)	0.0327 (4)
C3	0.8130 (2)	1.04027 (11)	0.09679 (15)	0.0337 (4)
N2	0.59270 (18)	0.80749 (10)	−0.01543 (13)	0.0375 (3)
C5	0.5327 (2)	0.73504 (12)	0.05823 (16)	0.0383 (4)
O2	0.54386 (18)	0.74213 (9)	0.18607 (12)	0.0526 (4)
C7	0.8664 (2)	1.12830 (12)	0.04435 (18)	0.0433 (4)
H7	0.8404	1.1384	−0.0537	0.052*
C8	0.8558 (2)	1.02813 (12)	0.24634 (16)	0.0377 (4)
C9	0.9474 (2)	1.10172 (13)	0.33407 (18)	0.0463 (4)
H9	0.9761	1.0928	0.4324	0.056*
C10	0.9563 (3)	1.20063 (13)	0.1329 (2)	0.0501 (5)
H10	0.9902	1.2586	0.0948	0.060*
C11	0.6710 (2)	0.97978 (13)	−0.15799 (16)	0.0434 (4)
H11A	0.7795	0.9752	−0.1935	0.065*
H11B	0.6180	1.0439	−0.1787	0.065*
H11C	0.5854	0.9306	−0.2030	0.065*
C12	0.9960 (2)	1.18695 (13)	0.27825 (19)	0.0489 (5)
H12	1.0562	1.2360	0.3385	0.059*
C13	0.4561 (3)	0.64741 (13)	−0.0270 (2)	0.0539 (5)
H13A	0.5521	0.6014	−0.0287	0.081*
H13B	0.4001	0.6674	−0.1227	0.081*
H13C	0.3666	0.6169	0.0152	0.081*
O1	0.81218 (19)	0.94621 (9)	0.31076 (11)	0.0531 (4)
H1	0.7625	0.9065	0.2500	0.080*
H2A	0.575 (2)	0.8027 (14)	−0.1101 (10)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0430 (8)	0.0360 (7)	0.0278 (6)	0.0011 (6)	0.0075 (5)	−0.0009 (5)
C2	0.0331 (8)	0.0379 (8)	0.0283 (7)	0.0082 (6)	0.0094 (6)	0.0022 (6)
C3	0.0342 (8)	0.0353 (8)	0.0324 (8)	0.0053 (6)	0.0096 (6)	0.0020 (6)
N2	0.0516 (8)	0.0379 (8)	0.0232 (6)	−0.0013 (6)	0.0089 (6)	−0.0016 (6)
C5	0.0454 (9)	0.0389 (9)	0.0320 (8)	0.0040 (7)	0.0119 (7)	0.0026 (7)
O2	0.0809 (9)	0.0502 (8)	0.0298 (6)	−0.0026 (6)	0.0192 (6)	0.0023 (5)
C7	0.0511 (10)	0.0420 (9)	0.0381 (8)	0.0014 (8)	0.0129 (7)	0.0057 (7)
C8	0.0411 (9)	0.0405 (9)	0.0323 (8)	0.0021 (7)	0.0101 (6)	0.0006 (7)
C9	0.0525 (10)	0.0519 (11)	0.0345 (8)	−0.0021 (8)	0.0100 (7)	−0.0070 (8)
C10	0.0576 (11)	0.0389 (9)	0.0560 (11)	−0.0049 (8)	0.0175 (9)	0.0026 (8)
C11	0.0547 (10)	0.0455 (9)	0.0294 (8)	0.0031 (8)	0.0085 (7)	0.0049 (7)
C12	0.0481 (10)	0.0463 (10)	0.0530 (10)	−0.0057 (8)	0.0129 (8)	−0.0131 (8)
C13	0.0718 (13)	0.0455 (10)	0.0475 (10)	−0.0097 (9)	0.0197 (9)	−0.0059 (8)
O1	0.0782 (9)	0.0507 (8)	0.0273 (6)	−0.0141 (6)	0.0060 (6)	0.0036 (5)

Geometric parameters (Å, º)

N1—C2	1.284 (2)	C8—C9	1.386 (2)
N1—N2	1.3641 (18)	C9—C12	1.363 (2)
C2—C3	1.470 (2)	C9—H9	0.9300
C2—C11	1.496 (2)	C10—C12	1.376 (3)
C3—C7	1.394 (2)	C10—H10	0.9300
C3—C8	1.412 (2)	C11—H11A	0.9600
N2—C5	1.3520 (19)	C11—H11B	0.9600
N2—H2A	0.894 (9)	C11—H11C	0.9600
C5—O2	1.2197 (19)	C12—H12	0.9300
C5—C13	1.486 (2)	C13—H13A	0.9600
C7—C10	1.373 (2)	C13—H13B	0.9600
C7—H7	0.9300	C13—H13C	0.9600
C8—O1	1.3520 (19)	O1—H1	0.8200
C2—N1—N2	121.70 (12)	C8—C9—H9	119.5
N1—C2—C3	115.17 (13)	C7—C10—C12	119.73 (16)
N1—C2—C11	124.28 (14)	C7—C10—H10	120.1
C3—C2—C11	120.55 (14)	C12—C10—H10	120.1
C7—C3—C8	116.98 (15)	C2—C11—H11A	109.5
C7—C3—C2	121.10 (14)	C2—C11—H11B	109.5
C8—C3—C2	121.92 (14)	H11A—C11—H11B	109.5
C5—N2—N1	117.09 (12)	C2—C11—H11C	109.5
C5—N2—H2A	119.6 (12)	H11A—C11—H11C	109.5
N1—N2—H2A	123.3 (12)	H11B—C11—H11C	109.5
O2—C5—N2	121.36 (15)	C9—C12—C10	120.14 (17)
O2—C5—C13	123.33 (15)	C9—C12—H12	119.9
N2—C5—C13	115.31 (13)	C10—C12—H12	119.9
C10—C7—C3	122.09 (15)	C5—C13—H13A	109.5
C10—C7—H7	119.0	C5—C13—H13B	109.5
C3—C7—H7	119.0	H13A—C13—H13B	109.5
O1—C8—C9	116.97 (14)	C5—C13—H13C	109.5
O1—C8—C3	122.88 (14)	H13A—C13—H13C	109.5
C9—C8—C3	120.15 (15)	H13B—C13—H13C	109.5
C12—C9—C8	120.92 (16)	C8—O1—H1	109.5
C12—C9—H9	119.5
N2—N1—C2—C3	−178.91 (13)	C2—C3—C7—C10	−179.66 (15)
N2—N1—C2—C11	1.9 (2)	C7—C3—C8—O1	−179.77 (15)
N1—C2—C3—C7	178.95 (14)	C2—C3—C8—O1	−0.3 (2)
C11—C2—C3—C7	−1.8 (2)	C7—C3—C8—C9	−0.2 (2)
N1—C2—C3—C8	−0.5 (2)	C2—C3—C8—C9	179.30 (14)
C11—C2—C3—C8	178.70 (14)	O1—C8—C9—C12	−179.73 (15)
C2—N1—N2—C5	−170.30 (13)	C3—C8—C9—C12	0.7 (3)
N1—N2—C5—O2	4.7 (2)	C3—C7—C10—C12	0.1 (3)
N1—N2—C5—C13	−174.46 (14)	C8—C9—C12—C10	−0.8 (3)
C8—C3—C7—C10	−0.2 (2)	C7—C10—C12—C9	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.81	2.5239 (18)	145
N2—H2A···O2^i	0.89 (1)	2.02 (1)	2.8951 (19)	167 (2)
C11—H11C···N2	0.96	2.45	2.845 (2)	104
C11—H11C···O2^i	0.96	2.57	3.406 (2)	146

Symmetry code: (i) x, −y+3/2, z−1/2.