N'-(2-Meth-oxy-benzyl-idene)aceto-hydrazide.

In the title mol-ecule, C(10)H(12)N(2)O(2), the acetohydrazide group is almost planar [within 0.0306 (12) Å] and forms a dihedral angle of 12.15 (14)° with the benzene ring. The meth-oxy group deviates from the attached benzene ring with a C-O-C-C torsion angle of 4.2 (4)°·The mol-ecule adopts a trans configuration with respect to the C=N bond. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of N-H⋯O hydrogen bonds and intermolecular C-H⋯O interactions further stabilize the structure.

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C10H12N2O2

M = 192.22

Triclinic,

a = 5.3865 (7) Å

b = 8.4609 (11) Å

c = 11.3301 (14) Å

α = 77.499 (4)°

β = 76.516 (5)°

γ = 89.101 (5)°

V = 489.90 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 223 K

0.19 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.982, T max = 0.985

4827 measured reflections

1694 independent reflections

1489 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.163

S = 1.06

1694 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 I, global. DOI: 10.1107/S1600536810038092/gw2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038092/gw2092Isup2.hkl

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

C10H12N2O2	Z = 2
Mr = 192.22	F(000) = 204
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3865 (7) Å	Cell parameters from 1694 reflections
b = 8.4609 (11) Å	θ = 1.9–25.0°
c = 11.3301 (14) Å	µ = 0.09 mm−1
α = 77.499 (4)°	T = 223 K
β = 76.516 (5)°	Block, colourless
γ = 89.101 (5)°	0.19 × 0.17 × 0.15 mm
V = 489.90 (11) Å3

Bruker SMART CCD area-detector diffractometer	1694 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
Tmin = 0.982, Tmax = 0.985	k = −10→9
4827 measured reflections	l = −13→13

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0812P)2 + 0.265P] where P = (Fo2 + 2Fc2)/3
1694 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.3030 (3)	0.1576 (2)	0.41553 (14)	0.0617 (5)
C10	0.6401 (4)	0.2210 (3)	−0.2060 (2)	0.0533 (6)
H10A	0.5000	0.2686	−0.1579	0.080*
H10B	0.5753	0.1429	−0.2424	0.080*
H10C	0.7390	0.3041	−0.2707	0.080*
N1	0.5212 (3)	0.2232 (2)	0.04470 (16)	0.0430 (5)
N2	0.7383 (3)	0.1459 (2)	−0.00176 (16)	0.0461 (5)
H2	0.8319	0.1014	0.0474	0.055*
C1	0.1048 (5)	0.3982 (3)	0.1500 (2)	0.0522 (6)
H1	0.1575	0.4195	0.0637	0.063*
C2	−0.1084 (5)	0.4724 (3)	0.2049 (2)	0.0576 (6)
H2A	−0.1987	0.5420	0.1560	0.069*
C3	−0.1852 (5)	0.4423 (3)	0.3321 (2)	0.0572 (6)
H3	−0.3285	0.4917	0.3696	0.069*
C4	−0.0514 (5)	0.3388 (3)	0.4053 (2)	0.0562 (6)
H4	−0.1048	0.3197	0.4915	0.067*
C5	0.1626 (4)	0.2634 (3)	0.3506 (2)	0.0462 (5)
C6	0.2348 (6)	0.1311 (4)	0.5483 (2)	0.0720 (8)
H6A	0.3527	0.0593	0.5823	0.108*
H6B	0.0651	0.0835	0.5791	0.108*
H6C	0.2408	0.2326	0.5725	0.108*
C7	0.2427 (4)	0.2924 (3)	0.22085 (19)	0.0418 (5)
C8	0.4680 (4)	0.2133 (3)	0.16151 (19)	0.0421 (5)
H8	0.5719	0.1559	0.2096	0.050*
C9	0.8059 (4)	0.1389 (3)	−0.12303 (19)	0.0424 (5)
O2	0.9982 (3)	0.0679 (2)	−0.16141 (14)	0.0528 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0686 (11)	0.0756 (12)	0.0348 (8)	0.0287 (9)	−0.0062 (7)	−0.0076 (8)
C10	0.0497 (13)	0.0723 (16)	0.0378 (12)	0.0158 (11)	−0.0097 (10)	−0.0134 (11)
N1	0.0414 (9)	0.0489 (11)	0.0373 (9)	0.0120 (7)	−0.0048 (7)	−0.0116 (8)
N2	0.0431 (10)	0.0589 (12)	0.0350 (9)	0.0181 (8)	−0.0073 (7)	−0.0107 (8)
C1	0.0573 (13)	0.0584 (14)	0.0412 (12)	0.0157 (11)	−0.0123 (10)	−0.0118 (10)
C2	0.0562 (14)	0.0611 (15)	0.0585 (15)	0.0213 (11)	−0.0178 (11)	−0.0166 (12)
C3	0.0508 (13)	0.0610 (15)	0.0602 (15)	0.0174 (11)	−0.0046 (11)	−0.0242 (12)
C4	0.0582 (14)	0.0650 (15)	0.0409 (12)	0.0131 (11)	0.0008 (10)	−0.0162 (11)
C5	0.0486 (12)	0.0489 (12)	0.0391 (11)	0.0084 (9)	−0.0070 (9)	−0.0098 (9)
C6	0.094 (2)	0.083 (2)	0.0359 (13)	0.0288 (16)	−0.0138 (13)	−0.0109 (12)
C7	0.0422 (11)	0.0440 (12)	0.0387 (11)	0.0064 (9)	−0.0070 (9)	−0.0114 (9)
C8	0.0447 (11)	0.0444 (11)	0.0360 (11)	0.0088 (9)	−0.0078 (9)	−0.0088 (9)
C9	0.0394 (11)	0.0494 (12)	0.0357 (11)	0.0065 (9)	−0.0039 (8)	−0.0091 (9)
O2	0.0479 (9)	0.0689 (11)	0.0396 (8)	0.0221 (7)	−0.0051 (7)	−0.0143 (7)

O1—C5	1.367 (3)	C2—C3	1.371 (3)
O1—C6	1.430 (3)	C2—H2A	0.9300
C10—C9	1.501 (3)	C3—C4	1.385 (4)
C10—H10A	0.9600	C3—H3	0.9300
C10—H10B	0.9600	C4—C5	1.391 (3)
C10—H10C	0.9600	C4—H4	0.9300
N1—C8	1.272 (3)	C5—C7	1.399 (3)
N1—N2	1.382 (2)	C6—H6A	0.9600
N2—C9	1.351 (3)	C6—H6B	0.9600
N2—H2	0.8600	C6—H6C	0.9600
C1—C2	1.383 (3)	C7—C8	1.470 (3)
C1—C7	1.394 (3)	C8—H8	0.9300
C1—H1	0.9300	C9—O2	1.227 (2)
C5—O1—C6	117.66 (19)	C3—C4—H4	119.8
C9—C10—H10A	109.5	C5—C4—H4	119.8
C9—C10—H10B	109.5	O1—C5—C4	124.3 (2)
H10A—C10—H10B	109.5	O1—C5—C7	116.03 (19)
C9—C10—H10C	109.5	C4—C5—C7	119.7 (2)
H10A—C10—H10C	109.5	O1—C6—H6A	109.5
H10B—C10—H10C	109.5	O1—C6—H6B	109.5
C8—N1—N2	115.56 (18)	H6A—C6—H6B	109.5
C9—N2—N1	121.13 (17)	O1—C6—H6C	109.5
C9—N2—H2	119.4	H6A—C6—H6C	109.5
N1—N2—H2	119.4	H6B—C6—H6C	109.5
C2—C1—C7	121.7 (2)	C1—C7—C5	118.4 (2)
C2—C1—H1	119.2	C1—C7—C8	121.2 (2)
C7—C1—H1	119.2	C5—C7—C8	120.42 (19)
C3—C2—C1	119.2 (2)	N1—C8—C7	120.22 (19)
C3—C2—H2A	120.4	N1—C8—H8	119.9
C1—C2—H2A	120.4	C7—C8—H8	119.9
C2—C3—C4	120.6 (2)	O2—C9—N2	119.71 (19)
C2—C3—H3	119.7	O2—C9—C10	122.64 (19)
C4—C3—H3	119.7	N2—C9—C10	117.65 (18)
C3—C4—C5	120.4 (2)
C8—N1—N2—C9	175.77 (19)	O1—C5—C7—C1	179.4 (2)
C7—C1—C2—C3	0.5 (4)	C4—C5—C7—C1	0.5 (4)
C1—C2—C3—C4	0.0 (4)	O1—C5—C7—C8	−0.9 (3)
C2—C3—C4—C5	−0.3 (4)	C4—C5—C7—C8	−179.8 (2)
C6—O1—C5—C4	−4.2 (4)	N2—N1—C8—C7	179.40 (17)
C6—O1—C5—C7	176.9 (2)	C1—C7—C8—N1	−9.4 (3)
C3—C4—C5—O1	−178.8 (2)	C5—C7—C8—N1	171.0 (2)
C3—C4—C5—C7	0.0 (4)	N1—N2—C9—O2	−179.23 (19)
C2—C1—C7—C5	−0.8 (4)	N1—N2—C9—C10	1.3 (3)
C2—C1—C7—C8	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N1	0.96	2.27	2.766 (3)	111
N2—H2···O2i	0.86	2.07	2.899 (2)	163
C6—H6A···O1ii	0.96	2.59	3.491 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.07	2.899 (2)	163
C6—H6A⋯O1ii	0.96	2.59	3.491 (3)	157

Symmetry codes: (i) ; (ii) .