N'-[1-(4-Methoxy-phen-yl)ethyl-idene]acetohydrazide.

The title compound, C(11)H(14)N(2)O(2), was prepared by the reaction of acetohydrazide and 1-(4-methoxy-phen-yl)ethanone. In the mol-ecule, all bond lengths and angles are within normal ranges. In the crystal structure, adjacent mol-ecules are linked into a centrosymmetric dimer by inter-molecular N-H⋯O hydrogen bonding.

Related literature

For related literature, see: Cimerman et al. (1997 ▶); Girgis (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14N2O2

M = 206.24

Monoclinic,

a = 13.282 (3) Å

b = 4.9923 (10) Å

c = 16.854 (3) Å

β = 98.88 (3)°

V = 1104.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

6830 measured reflections

2681 independent reflections

1228 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.196

S = 0.93

2681 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037677/at2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037677/at2657Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H14N2O2	F000 = 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 = 2.4–24.0º
b = 4.9923 (10) Å	µ = 0.09 mm−1
c = 16.854 (3) Å	T = 293 (2) K
β = 98.88 (3)º	Block, yellow
V = 1104.2 (4) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Monochromator: graphite	θmax = 28.3º
T = 273(2) K	θmin = 1.8º
φ and ω scans	h = −17→15
Absorption correction: none	k = −6→6
6830 measured reflections	l = −16→22
2681 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.196	w = 1/[σ2(Fo2) + (0.0986P)2 + 0.0719P] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2681 reflections	Δρmax = 0.17 e Å−3
137 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .