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

The mol-ecule of the title compound, C(12)H(16)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 13.82 (6)°. In the crystal structure, mol-ecules are linked into centrosymmetric dimers by N-H⋯O and C-H⋯O hydrogen bonds, and the dimers are linked together by C-H⋯π inter-actions.

Related literature

For general background, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For a related structure, see: Lv et al. (2008 ▶).

Experimental

Crystal data

C12H16N2O3

M = 236.27

Orthorhombic,

a = 12.1020 (11) Å

b = 8.1727 (7) Å

c = 25.476 (2) Å

V = 2519.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 123 (2) K

0.27 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2002 ▶) T min = 0.973, T max = 0.981

12848 measured reflections

2222 independent reflections

1845 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.127

S = 1.07

2222 reflections

158 parameters

H-atom parameters constrained

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/S1600536808031462/ci2686sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031462/ci2686Isup2.hkl

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

C12H16N2O3	F(000) = 1008
Mr = 236.27	Dx = 1.246 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2222 reflections
a = 12.1020 (11) Å	θ = 1.6–25.0°
b = 8.1727 (7) Å	µ = 0.09 mm−1
c = 25.476 (2) Å	T = 123 K
V = 2519.8 (4) Å3	Block, colourless
Z = 8	0.27 × 0.23 × 0.22 mm

Bruker SMART CCD area-detector diffractometer	2222 independent reflections
Radiation source: fine-focus sealed tube	1845 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS, Bruker, 2002)	h = −12→14
Tmin = 0.973, Tmax = 0.981	k = −9→9
12848 measured reflections	l = −30→30

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.6384P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
2222 reflections	Δρmax = 0.19 e Å−3
158 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (13)

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
C7	0.42346 (13)	0.5640 (2)	0.60487 (6)	0.0490 (4)
C8	0.43416 (13)	0.4210 (2)	0.56947 (6)	0.0501 (4)
C3	0.40760 (13)	0.8369 (2)	0.67166 (6)	0.0525 (4)
C2	0.37209 (14)	0.8477 (2)	0.62024 (7)	0.0570 (4)
H2	0.3430	0.9453	0.6075	0.068*
C9	0.59258 (14)	0.0586 (2)	0.56465 (7)	0.0542 (4)
C5	0.45905 (15)	0.5568 (2)	0.65717 (7)	0.0580 (5)
H5	0.4890	0.4600	0.6700	0.070*
C6	0.38006 (15)	0.7122 (2)	0.58781 (6)	0.0561 (4)
H6	0.3555	0.7207	0.5533	0.067*
C4	0.45058 (16)	0.6900 (2)	0.68974 (7)	0.0613 (5)
H4	0.4740	0.6816	0.7244	0.074*
C1	0.35816 (19)	1.1125 (2)	0.69025 (8)	0.0733 (6)
H1A	0.4039	1.1577	0.6631	0.110*
H1B	0.3550	1.1872	0.7193	0.110*
H1C	0.2850	1.0948	0.6769	0.110*
C11	0.7327 (2)	−0.0352 (3)	0.68377 (9)	0.0932 (7)
H11A	0.7656	0.0694	0.6908	0.140*
H11B	0.7815	−0.1204	0.6954	0.140*
H11C	0.6637	−0.0435	0.7021	0.140*
C10	0.7136 (2)	−0.0522 (3)	0.62760 (9)	0.0894 (8)
H10A	0.6803	−0.1576	0.6201	0.107*
H10B	0.7831	−0.0451	0.6087	0.107*
O3	0.63987 (11)	0.07917 (16)	0.61102 (5)	0.0677 (4)
O2	0.61004 (11)	−0.05717 (16)	0.53593 (5)	0.0701 (4)
O1	0.40315 (12)	0.96202 (16)	0.70721 (5)	0.0673 (4)
N2	0.52061 (12)	0.17888 (17)	0.55187 (5)	0.0571 (4)
H2A	0.4835	0.1713	0.5232	0.068*
N1	0.50534 (12)	0.31305 (17)	0.58366 (5)	0.0532 (4)
C12	0.36482 (15)	0.4117 (2)	0.52056 (7)	0.0621 (5)
H12A	0.4098	0.4361	0.4905	0.093*
H12B	0.3056	0.4896	0.5228	0.093*
H12C	0.3347	0.3036	0.5171	0.093*

	U11	U22	U33	U12	U13	U23
C7	0.0429 (8)	0.0533 (9)	0.0509 (9)	−0.0002 (7)	0.0003 (7)	0.0052 (7)
C8	0.0451 (9)	0.0546 (10)	0.0505 (9)	−0.0011 (7)	0.0025 (7)	0.0067 (7)
C3	0.0468 (9)	0.0571 (10)	0.0536 (9)	−0.0019 (8)	0.0000 (7)	−0.0028 (7)
C2	0.0595 (10)	0.0542 (10)	0.0572 (9)	0.0087 (8)	−0.0028 (8)	0.0067 (8)
C9	0.0501 (9)	0.0571 (10)	0.0555 (9)	0.0012 (8)	−0.0014 (7)	−0.0050 (8)
C5	0.0597 (10)	0.0560 (10)	0.0584 (10)	0.0046 (8)	−0.0103 (8)	0.0079 (8)
C6	0.0606 (10)	0.0615 (11)	0.0461 (8)	0.0065 (8)	−0.0038 (7)	0.0049 (8)
C4	0.0642 (11)	0.0664 (11)	0.0532 (9)	0.0029 (9)	−0.0134 (8)	0.0029 (8)
C1	0.0867 (14)	0.0597 (12)	0.0736 (12)	0.0091 (10)	−0.0031 (10)	−0.0111 (10)
C11	0.1006 (18)	0.0890 (16)	0.0900 (15)	0.0101 (14)	−0.0275 (13)	0.0137 (13)
C10	0.0913 (17)	0.0877 (16)	0.0894 (15)	0.0396 (13)	−0.0261 (12)	−0.0145 (12)
O3	0.0734 (9)	0.0651 (8)	0.0646 (8)	0.0184 (6)	−0.0172 (6)	−0.0106 (6)
O2	0.0664 (8)	0.0722 (9)	0.0715 (8)	0.0159 (7)	−0.0101 (6)	−0.0200 (7)
O1	0.0760 (9)	0.0648 (8)	0.0611 (7)	0.0067 (6)	−0.0071 (6)	−0.0088 (6)
N2	0.0598 (8)	0.0592 (9)	0.0522 (8)	0.0075 (7)	−0.0079 (6)	−0.0035 (6)
N1	0.0563 (8)	0.0512 (8)	0.0520 (8)	0.0021 (6)	−0.0004 (6)	−0.0005 (6)
C12	0.0575 (10)	0.0676 (12)	0.0613 (10)	0.0027 (9)	−0.0066 (8)	−0.0046 (9)

C7—C6	1.390 (2)	C1—O1	1.412 (2)
C7—C5	1.401 (2)	C1—H1A	0.96
C7—C8	1.482 (2)	C1—H1B	0.96
C8—N1	1.285 (2)	C1—H1C	0.96
C8—C12	1.504 (2)	C11—C10	1.456 (3)
C3—O1	1.367 (2)	C11—H11A	0.96
C3—C2	1.382 (2)	C11—H11B	0.96
C3—C4	1.387 (2)	C11—H11C	0.96
C2—C6	1.385 (2)	C10—O3	1.458 (2)
C2—H2	0.93	C10—H10A	0.97
C9—O2	1.215 (2)	C10—H10B	0.97
C9—O3	1.323 (2)	N2—N1	1.376 (2)
C9—N2	1.353 (2)	N2—H2A	0.86
C5—C4	1.372 (2)	C12—H12A	0.96
C5—H5	0.93	C12—H12B	0.96
C6—H6	0.93	C12—H12C	0.96
C4—H4	0.93
C6—C7—C5	116.71 (15)	O1—C1—H1C	109.5
C6—C7—C8	122.01 (14)	H1A—C1—H1C	109.5
C5—C7—C8	121.27 (15)	H1B—C1—H1C	109.5
N1—C8—C7	115.38 (14)	C10—C11—H11A	109.5
N1—C8—C12	124.94 (15)	C10—C11—H11B	109.5
C7—C8—C12	119.67 (14)	H11A—C11—H11B	109.5
O1—C3—C2	124.64 (16)	C10—C11—H11C	109.5
O1—C3—C4	116.25 (15)	H11A—C11—H11C	109.5
C2—C3—C4	119.11 (16)	H11B—C11—H11C	109.5
C3—C2—C6	119.53 (16)	C11—C10—O3	108.19 (18)
C3—C2—H2	120.2	C11—C10—H10A	110.1
C6—C2—H2	120.2	O3—C10—H10A	110.1
O2—C9—O3	124.14 (16)	C11—C10—H10B	110.1
O2—C9—N2	122.21 (16)	O3—C10—H10B	110.1
O3—C9—N2	113.64 (14)	H10A—C10—H10B	108.4
C4—C5—C7	121.26 (16)	C9—O3—C10	115.45 (14)
C4—C5—H5	119.4	C3—O1—C1	117.62 (14)
C7—C5—H5	119.4	C9—N2—N1	121.58 (14)
C2—C6—C7	122.46 (15)	C9—N2—H2A	119.2
C2—C6—H6	118.8	N1—N2—H2A	119.2
C7—C6—H6	118.8	C8—N1—N2	118.13 (14)
C5—C4—C3	120.91 (16)	C8—C12—H12A	109.5
C5—C4—H4	119.5	C8—C12—H12B	109.5
C3—C4—H4	119.5	H12A—C12—H12B	109.5
O1—C1—H1A	109.5	C8—C12—H12C	109.5
O1—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.10	2.914 (2)	157
C12—H12C···O2i	0.96	2.52	3.250 (2)	133
C1—H1C···Cg1ii	0.96	2.76	3.637 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.10	2.914 (2)	157
C12—H12C⋯O2i	0.96	2.52	3.250 (2)	133
C1—H1C⋯Cg1ii	0.96	2.76	3.637 (2)	153

Symmetry codes: (i) ; (ii) .