The title compound, C
11H
14N
2O
2, was prepared by the reaction of acetohydrazide and 1-(4-methoxyphenyl)ethanone. In the molecule, all bond lengths and angles are within normal ranges. In the crystal structure, adjacent molecules are linked into a centrosymmetric dimer by intermolecular N—H

O hydrogen bonding.
Supporting information
CCDC reference: 712505
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.196
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C
Value of measurement temperature given = 293.000
Value of melting point given = 0.000
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.14 Ratio
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C11 H14 N2 O2
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
A mixture of the acetohydrazide (0.1 mol), and 1-(4-methoxyphenyl)ethanone (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title
compound (0.080 mol, yield 80%). Single crystals suitable for X-ray
measurements were obtained by recrystallization from ethanol at room
temperature.
H atoms were fixed geometrically and allowed to ride on their attached atoms,
with C—H = 0.93-0.96 Å and N—H = 0.86 Å, and with
Uiso=1.2–1.5Ueq.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
N'-[1-(4-Methoxyphenyl)ethylidene]acetohydrazide
top
Crystal data top
C11H14N2O2 | F(000) = 440 |
Mr = 206.24 | Dx = 1.241 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 831 reflections |
a = 13.282 (3) Å | θ = 2.4–24.0° |
b = 4.9923 (10) Å | µ = 0.09 mm−1 |
c = 16.854 (3) Å | T = 293 K |
β = 98.88 (3)° | Block, yellow |
V = 1104.2 (4) Å3 | 0.25 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1228 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
ϕ and ω scans | h = −17→15 |
6830 measured reflections | k = −6→6 |
2681 independent reflections | l = −16→22 |
Refinement top
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0986P)2 + 0.0719P] where P = (Fo2 + 2Fc2)/3 |
2681 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Crystal data top
C11H14N2O2 | V = 1104.2 (4) Å3 |
Mr = 206.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.282 (3) Å | µ = 0.09 mm−1 |
b = 4.9923 (10) Å | T = 293 K |
c = 16.854 (3) Å | 0.25 × 0.20 × 0.18 mm |
β = 98.88 (3)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1228 reflections with I > 2σ(I) |
6830 measured reflections | Rint = 0.035 |
2681 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.17 e Å−3 |
2681 reflections | Δρmin = −0.17 e Å−3 |
137 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 | x | y | z | Uiso*/Ueq | |
O2 | 0.98272 (13) | 0.2016 (4) | 0.91643 (10) | 0.0761 (6) | |
O1 | 1.64324 (12) | 0.8045 (4) | 1.19345 (10) | 0.0788 (6) | |
N2 | 1.12429 (14) | 0.2219 (4) | 1.00666 (11) | 0.0631 (6) | |
H2A | 1.1037 | 0.0925 | 1.0338 | 0.076* | |
N1 | 1.21780 (14) | 0.3415 (4) | 1.03226 (11) | 0.0608 (5) | |
C5 | 1.36778 (17) | 0.4053 (4) | 1.12310 (13) | 0.0559 (6) | |
C10 | 1.06577 (19) | 0.3085 (5) | 0.93934 (14) | 0.0606 (6) | |
C8 | 1.26860 (17) | 0.2683 (4) | 1.09940 (13) | 0.0572 (6) | |
C2 | 1.55227 (16) | 0.6811 (5) | 1.16686 (13) | 0.0588 (6) | |
C7 | 1.51710 (18) | 0.5048 (5) | 1.21885 (14) | 0.0675 (7) | |
H7A | 1.5547 | 0.4775 | 1.2695 | 0.081* | |
C3 | 1.49509 (19) | 0.7215 (5) | 1.09293 (15) | 0.0739 (8) | |
H3A | 1.5174 | 0.8408 | 1.0570 | 0.089* | |
C4 | 1.40476 (19) | 0.5860 (6) | 1.07177 (14) | 0.0752 (8) | |
H4A | 1.3671 | 0.6163 | 1.0213 | 0.090* | |
C6 | 1.42740 (18) | 0.3683 (5) | 1.19720 (13) | 0.0632 (7) | |
H6A | 1.4061 | 0.2477 | 1.2333 | 0.076* | |
C11 | 1.1030 (2) | 0.5331 (5) | 0.89359 (15) | 0.0754 (7) | |
H11A | 1.0532 | 0.5729 | 0.8475 | 0.113* | |
H11B | 1.1660 | 0.4828 | 0.8764 | 0.113* | |
H11C | 1.1137 | 0.6886 | 0.9273 | 0.113* | |
C9 | 1.2343 (2) | 0.0599 (6) | 1.15380 (17) | 0.0931 (10) | |
H9A | 1.1689 | 0.1090 | 1.1668 | 0.159 (16)* | |
H9B | 1.2828 | 0.0482 | 1.2022 | 0.239* | |
H9C | 1.2292 | −0.1105 | 1.1271 | 0.239* | |
C1 | 1.68123 (19) | 0.9957 (5) | 1.14314 (16) | 0.0807 (8) | |
H1B | 1.7453 | 1.0639 | 1.1695 | 0.121* | |
H1C | 1.6335 | 1.1404 | 1.1324 | 0.121* | |
H1D | 1.6906 | 0.9120 | 1.0935 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0790 (12) | 0.0801 (12) | 0.0670 (11) | −0.0227 (10) | 0.0048 (9) | 0.0087 (9) |
O1 | 0.0687 (11) | 0.0908 (13) | 0.0735 (12) | −0.0172 (10) | 0.0003 (9) | 0.0073 (10) |
N2 | 0.0729 (13) | 0.0604 (12) | 0.0562 (12) | −0.0161 (10) | 0.0109 (10) | 0.0038 (9) |
N1 | 0.0651 (12) | 0.0615 (12) | 0.0562 (12) | −0.0126 (9) | 0.0107 (9) | −0.0025 (9) |
C5 | 0.0640 (13) | 0.0541 (13) | 0.0515 (13) | −0.0032 (11) | 0.0153 (11) | −0.0005 (10) |
C10 | 0.0718 (16) | 0.0557 (14) | 0.0558 (14) | −0.0084 (12) | 0.0145 (12) | −0.0020 (11) |
C8 | 0.0674 (15) | 0.0560 (14) | 0.0506 (13) | −0.0047 (12) | 0.0162 (11) | −0.0009 (11) |
C2 | 0.0598 (14) | 0.0620 (14) | 0.0549 (13) | 0.0000 (11) | 0.0097 (11) | 0.0000 (11) |
C7 | 0.0722 (15) | 0.0773 (16) | 0.0510 (13) | −0.0031 (14) | 0.0033 (11) | 0.0059 (12) |
C3 | 0.0746 (16) | 0.0863 (19) | 0.0598 (15) | −0.0177 (15) | 0.0072 (13) | 0.0196 (14) |
C4 | 0.0759 (16) | 0.0917 (19) | 0.0542 (14) | −0.0197 (15) | −0.0016 (12) | 0.0178 (13) |
C6 | 0.0768 (16) | 0.0603 (14) | 0.0533 (14) | −0.0024 (12) | 0.0130 (12) | 0.0081 (11) |
C11 | 0.0877 (17) | 0.0683 (16) | 0.0696 (16) | −0.0160 (14) | 0.0099 (13) | 0.0132 (13) |
C9 | 0.101 (2) | 0.097 (2) | 0.0798 (19) | −0.0350 (18) | 0.0105 (16) | 0.0259 (17) |
C1 | 0.0726 (16) | 0.0842 (19) | 0.0872 (18) | −0.0190 (15) | 0.0183 (14) | 0.0019 (16) |
Geometric parameters (Å, º) top
O2—C10 | 1.232 (3) | C7—H7A | 0.9300 |
O1—C2 | 1.369 (3) | C3—C4 | 1.376 (3) |
O1—C1 | 1.420 (3) | C3—H3A | 0.9300 |
N2—C10 | 1.344 (3) | C4—H4A | 0.9300 |
N2—N1 | 1.386 (2) | C6—H6A | 0.9300 |
N2—H2A | 0.8600 | C11—H11A | 0.9600 |
N1—C8 | 1.278 (3) | C11—H11B | 0.9600 |
C5—C6 | 1.384 (3) | C11—H11C | 0.9600 |
C5—C4 | 1.391 (3) | C9—H9A | 0.9600 |
C5—C8 | 1.483 (3) | C9—H9B | 0.9600 |
C10—C11 | 1.488 (3) | C9—H9C | 0.9600 |
C8—C9 | 1.503 (3) | C1—H1B | 0.9600 |
C2—C3 | 1.370 (3) | C1—H1C | 0.9600 |
C2—C7 | 1.374 (3) | C1—H1D | 0.9600 |
C7—C6 | 1.372 (3) | | |
| | | |
C2—O1—C1 | 118.96 (19) | C3—C4—H4A | 118.8 |
C10—N2—N1 | 119.9 (2) | C5—C4—H4A | 118.8 |
C10—N2—H2A | 120.1 | C7—C6—C5 | 121.7 (2) |
N1—N2—H2A | 120.1 | C7—C6—H6A | 119.1 |
C8—N1—N2 | 118.54 (19) | C5—C6—H6A | 119.1 |
C6—C5—C4 | 116.1 (2) | C10—C11—H11A | 109.5 |
C6—C5—C8 | 122.8 (2) | C10—C11—H11B | 109.5 |
C4—C5—C8 | 121.0 (2) | H11A—C11—H11B | 109.5 |
O2—C10—N2 | 119.9 (2) | C10—C11—H11C | 109.5 |
O2—C10—C11 | 121.1 (2) | H11A—C11—H11C | 109.5 |
N2—C10—C11 | 119.0 (2) | H11B—C11—H11C | 109.5 |
N1—C8—C5 | 115.6 (2) | C8—C9—H9A | 109.5 |
N1—C8—C9 | 124.7 (2) | C8—C9—H9B | 109.5 |
C5—C8—C9 | 119.7 (2) | H9A—C9—H9B | 109.5 |
O1—C2—C3 | 124.7 (2) | C8—C9—H9C | 109.5 |
O1—C2—C7 | 116.7 (2) | H9A—C9—H9C | 109.5 |
C3—C2—C7 | 118.6 (2) | H9B—C9—H9C | 109.5 |
C6—C7—C2 | 121.0 (2) | O1—C1—H1B | 109.5 |
C6—C7—H7A | 119.5 | O1—C1—H1C | 109.5 |
C2—C7—H7A | 119.5 | H1B—C1—H1C | 109.5 |
C2—C3—C4 | 120.1 (2) | O1—C1—H1D | 109.5 |
C2—C3—H3A | 119.9 | H1B—C1—H1D | 109.5 |
C4—C3—H3A | 119.9 | H1C—C1—H1D | 109.5 |
C3—C4—C5 | 122.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.12 | 2.956 (3) | 166 |
C4—H4A···N1 | 0.93 | 2.44 | 2.755 (3) | 100 |
Symmetry code: (i) −x+2, −y, −z+2. |
Experimental details
Crystal data |
Chemical formula | C11H14N2O2 |
Mr | 206.24 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.282 (3), 4.9923 (10), 16.854 (3) |
β (°) | 98.88 (3) |
V (Å3) | 1104.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6830, 2681, 1228 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.666 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.196, 0.93 |
No. of reflections | 2681 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.12 | 2.956 (3) | 166 |
Symmetry code: (i) −x+2, −y, −z+2. |
Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here.
In the title compound (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The C8—N1 bond length of 1.278 (3)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006).
In the crystal structure, adjacent molecules are linked into a centro-symmetric supra-molecular dimer by intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2).