(E)-Methyl N'-[1-(4-methoxy-phen-yl)ethyl-idene]hydrazinecarboxyl-ate.

The mol-ecule of the title compound, C(11)H(14)N(2)O(3), adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the hydrazinecarboxyl-ate plane is 12.06 (9)°. Mol-ecules are linked into a one-dimensional network by N-H⋯O hydrogen bonds and C-H⋯π inter-actions. The benzene rings of inversion-related mol-ecules are stacked with their centroids separated by 3.777 (1) Å, indicating π-π inter-actions.

Related literature

For general background, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For related structures, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Monoclinic,

a = 12.416 (3) Å

b = 11.113 (3) Å

c = 8.073 (2) Å

β = 95.628 (3)°

V = 1108.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.30 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.972, T max = 0.978

7124 measured reflections

1952 independent reflections

1624 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.07

1952 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.14 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/S1600536808024264/zl2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024264/zl2130Isup2.hkl

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

C11H14N2O3	F000 = 472
Mr = 222.24	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1952 reflections
a = 12.416 (3) Å	θ = 1.6–25.0º
b = 11.113 (3) Å	µ = 0.10 mm−1
c = 8.073 (2) Å	T = 273 (2) K
β = 95.628 (3)º	Block, colourless
V = 1108.5 (5) Å3	0.30 × 0.26 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1952 independent reflections
Radiation source: fine-focus sealed tube	1624 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −14→14
Tmin = 0.972, Tmax = 0.978	k = −13→11
7124 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.2826P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.19 e Å−3
1952 reflections	Δρmin = −0.14 e Å−3
153 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)
Secondary atom site location: difference Fourier map

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
H2A	0.6796 (14)	0.1822 (17)	0.308 (2)	0.059 (5)*
C7	0.96977 (11)	0.12453 (12)	0.16378 (16)	0.0297 (3)
C8	0.85779 (11)	0.12580 (12)	0.21369 (16)	0.0317 (3)
C10	0.62251 (11)	0.29834 (13)	0.14528 (18)	0.0348 (3)
C3	1.18244 (11)	0.12536 (13)	0.07457 (18)	0.0341 (3)
C5	1.04408 (11)	0.03686 (13)	0.22113 (17)	0.0351 (4)
H5	1.0223	−0.0236	0.2902	0.042*
C6	1.00522 (11)	0.21282 (12)	0.05809 (17)	0.0348 (4)
H6	0.9574	0.2727	0.0174	0.042*
C2	1.14990 (11)	0.03671 (13)	0.17850 (18)	0.0375 (4)
H2	1.1983	−0.0225	0.2196	0.045*
C4	1.10911 (11)	0.21306 (13)	0.01308 (18)	0.0364 (4)
H4	1.1305	0.2720	−0.0587	0.044*
C1	1.36336 (12)	0.05169 (17)	0.0921 (2)	0.0551 (5)
H1A	1.3691	0.0574	0.2113	0.083*
H1B	1.4320	0.0704	0.0531	0.083*
H1C	1.3425	−0.0286	0.0588	0.083*
C11	0.44286 (12)	0.36579 (16)	0.1528 (2)	0.0528 (5)
H11A	0.4628	0.4492	0.1589	0.079*
H11B	0.3810	0.3529	0.2132	0.079*
H11C	0.4254	0.3433	0.0385	0.079*
O1	1.28412 (8)	0.13431 (10)	0.02268 (14)	0.0460 (3)
O3	0.53202 (8)	0.29346 (10)	0.22464 (14)	0.0467 (3)
O2	0.63408 (8)	0.36576 (10)	0.03058 (13)	0.0432 (3)
N1	0.79718 (9)	0.21424 (11)	0.15959 (14)	0.0350 (3)
N2	0.69424 (10)	0.21707 (12)	0.21353 (17)	0.0391 (3)
C9	0.82244 (12)	0.02704 (14)	0.3229 (2)	0.0439 (4)
H9A	0.8329	0.0521	0.4372	0.066*
H9B	0.8646	−0.0439	0.3082	0.066*
H9C	0.7472	0.0098	0.2933	0.066*

	U11	U22	U33	U12	U13	U23
C7	0.0318 (7)	0.0303 (7)	0.0271 (7)	−0.0005 (5)	0.0034 (5)	−0.0038 (5)
C8	0.0343 (7)	0.0334 (8)	0.0277 (7)	−0.0011 (6)	0.0052 (5)	−0.0037 (6)
C10	0.0317 (7)	0.0391 (8)	0.0346 (8)	0.0006 (6)	0.0082 (6)	−0.0059 (7)
C3	0.0301 (7)	0.0370 (8)	0.0357 (8)	0.0004 (6)	0.0048 (6)	−0.0050 (6)
C5	0.0388 (8)	0.0333 (8)	0.0336 (8)	0.0002 (6)	0.0058 (6)	0.0038 (6)
C6	0.0342 (7)	0.0328 (8)	0.0374 (8)	0.0051 (6)	0.0041 (6)	0.0021 (6)
C2	0.0362 (8)	0.0357 (8)	0.0403 (8)	0.0086 (6)	0.0021 (6)	0.0019 (6)
C4	0.0361 (8)	0.0354 (8)	0.0386 (8)	−0.0008 (6)	0.0079 (6)	0.0049 (6)
C1	0.0332 (8)	0.0649 (12)	0.0680 (12)	0.0125 (8)	0.0084 (8)	0.0035 (9)
C11	0.0314 (8)	0.0592 (11)	0.0684 (12)	0.0078 (7)	0.0075 (7)	0.0000 (9)
O1	0.0304 (5)	0.0522 (7)	0.0565 (7)	0.0053 (5)	0.0107 (5)	0.0060 (5)
O3	0.0316 (5)	0.0567 (7)	0.0539 (7)	0.0066 (5)	0.0153 (5)	0.0079 (5)
O2	0.0425 (6)	0.0493 (7)	0.0396 (6)	0.0093 (5)	0.0125 (5)	0.0054 (5)
N1	0.0308 (6)	0.0412 (7)	0.0345 (7)	0.0028 (5)	0.0097 (5)	0.0002 (5)
N2	0.0330 (6)	0.0467 (8)	0.0393 (7)	0.0047 (5)	0.0131 (5)	0.0059 (6)
C9	0.0379 (8)	0.0442 (9)	0.0516 (9)	0.0011 (7)	0.0144 (7)	0.0075 (7)

C7—C5	1.3896 (19)	C2—H2	0.9300
C7—C6	1.399 (2)	C4—H4	0.9300
C7—C8	1.4850 (19)	C1—O1	1.4201 (19)
C8—N1	1.2878 (18)	C1—H1A	0.9600
C8—C9	1.500 (2)	C1—H1B	0.9600
C10—O2	1.2105 (17)	C1—H1C	0.9600
C10—N2	1.3476 (19)	C11—O3	1.4429 (19)
C10—O3	1.3479 (17)	C11—H11A	0.9600
C3—O1	1.3722 (17)	C11—H11B	0.9600
C3—C2	1.380 (2)	C11—H11C	0.9600
C3—C4	1.392 (2)	N1—N2	1.3905 (16)
C5—C2	1.390 (2)	N2—H2A	0.891 (19)
C5—H5	0.9300	C9—H9A	0.9600
C6—C4	1.3740 (19)	C9—H9B	0.9600
C6—H6	0.9300	C9—H9C	0.9600
C5—C7—C6	117.16 (13)	O1—C1—H1A	109.5
C5—C7—C8	121.66 (12)	O1—C1—H1B	109.5
C6—C7—C8	121.18 (12)	H1A—C1—H1B	109.5
N1—C8—C7	116.53 (12)	O1—C1—H1C	109.5
N1—C8—C9	124.24 (13)	H1A—C1—H1C	109.5
C7—C8—C9	119.23 (12)	H1B—C1—H1C	109.5
O2—C10—N2	127.18 (13)	O3—C11—H11A	109.5
O2—C10—O3	123.74 (13)	O3—C11—H11B	109.5
N2—C10—O3	109.08 (13)	H11A—C11—H11B	109.5
O1—C3—C2	124.78 (13)	O3—C11—H11C	109.5
O1—C3—C4	115.44 (13)	H11A—C11—H11C	109.5
C2—C3—C4	119.78 (13)	H11B—C11—H11C	109.5
C7—C5—C2	122.07 (13)	C3—O1—C1	117.08 (12)
C7—C5—H5	119.0	C10—O3—C11	115.40 (12)
C2—C5—H5	119.0	C8—N1—N2	115.82 (12)
C4—C6—C7	121.48 (13)	C10—N2—N1	118.55 (13)
C4—C6—H6	119.3	C10—N2—H2A	117.4 (12)
C7—C6—H6	119.3	N1—N2—H2A	122.0 (11)
C3—C2—C5	119.33 (13)	C8—C9—H9A	109.5
C3—C2—H2	120.3	C8—C9—H9B	109.5
C5—C2—H2	120.3	H9A—C9—H9B	109.5
C6—C4—C3	120.17 (13)	C8—C9—H9C	109.5
C6—C4—H4	119.9	H9A—C9—H9C	109.5
C3—C4—H4	119.9	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.89 (2)	2.01 (2)	2.8864 (17)	169.0
C4—H4···Cg1ii	0.93	2.87	3.6488 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.89 (2)	2.01 (2)	2.8864 (17)	169.0
C4—H4⋯Cg1ii	0.93	2.87	3.6488 (19)	142

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the benzene ring.