(E)-Methyl N'-(2-hydr-oxy-3-methoxy-benzyl-idene)hydrazinecarboxyl-ate.

The title compound, C(10)H(12)N(2)O(4), adopts a trans configuration with respect to the C=N double bond. The non-H atoms of the mol-ecule are essentially coplanar, with a maximum deviation of 0.015 (2) Å. An intra-molecular O-H⋯N inter-action is observed. In the crystal structure, the mol-ecules are linked into a two-dimensional network parallel to the ac plane by N-H⋯O hydrogen bonds involving the meth-oxy O atom and by two C-H⋯O hydrogen bonds involving the carbonyl O atom. In addition, an intermolecular C-H⋯π inter-action is observed.

Related literature

For general background to the properties of benzaldehyde­hydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For the use of metal complexes of Schiff bases as model compounds of active centres in various proteins and enzymes, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For a related structure, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C10H12N2O4

M = 224.22

Monoclinic,

a = 11.4348 (13) Å

b = 14.8717 (18) Å

c = 6.3508 (8) Å

β = 98.538 (4)°

V = 1068.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 223 K

0.24 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.975, T max = 0.985

5851 measured reflections

1049 independent reflections

948 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.11

1049 reflections

148 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.13 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/S1600536809021631/ci2816sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021631/ci2816Isup2.hkl

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

C10H12N2O4	F(000) = 472
Mr = 224.22	Dx = 1.394 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1049 reflections
a = 11.4348 (13) Å	θ = 2.3–26.0°
b = 14.8717 (18) Å	µ = 0.11 mm−1
c = 6.3508 (8) Å	T = 223 K
β = 98.538 (4)°	Block, colourles
V = 1068.0 (2) Å3	0.24 × 0.22 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1049 independent reflections
Radiation source: fine-focus sealed tube	948 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
Tmin = 0.975, Tmax = 0.985	k = −16→18
5851 measured reflections	l = −7→7

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.1415P] where P = (Fo2 + 2Fc2)/3
1049 reflections	(Δ/σ)max = 0.003
148 parameters	Δρmax = 0.11 e Å−3
2 restraints	Δρmin = −0.13 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
C1	0.11401 (17)	0.33419 (13)	0.6468 (3)	0.0412 (5)
C2	0.14440 (19)	0.38079 (15)	0.4705 (4)	0.0446 (5)
C3	0.0578 (2)	0.42357 (16)	0.3309 (4)	0.0513 (6)
H3	0.0779	0.4550	0.2149	0.062*
C4	−0.0596 (2)	0.4195 (2)	0.3646 (4)	0.0584 (6)
H4	−0.1176	0.4484	0.2704	0.070*
C5	−0.0906 (2)	0.37377 (16)	0.5339 (4)	0.0528 (6)
H5	−0.1696	0.3711	0.5531	0.063*
C6	−0.00420 (19)	0.33056 (15)	0.6795 (3)	0.0436 (5)
C7	−0.04116 (18)	0.28326 (16)	0.8601 (3)	0.0469 (5)
H7	−0.1203	0.2836	0.8788	0.056*
C8	0.07691 (19)	0.15569 (15)	1.3010 (3)	0.0451 (5)
C9	0.1022 (3)	0.0689 (2)	1.6128 (5)	0.0690 (8)
H9A	0.1535	0.0304	1.5467	0.103*
H9B	0.0569	0.0334	1.6977	0.103*
H9C	0.1487	0.1118	1.7019	0.103*
C10	0.2979 (3)	0.4277 (2)	0.2805 (5)	0.0767 (9)
H10A	0.2597	0.4021	0.1495	0.115*
H10B	0.3821	0.4231	0.2868	0.115*
H10C	0.2760	0.4898	0.2874	0.115*
N1	0.03469 (15)	0.24138 (13)	0.9926 (3)	0.0462 (4)
N2	−0.00459 (16)	0.19813 (14)	1.1600 (3)	0.0502 (5)
H2	−0.0782	0.1981	1.1743	0.060*
O1	0.20402 (14)	0.29467 (12)	0.7790 (3)	0.0553 (4)
H1	0.1776	0.2697	0.8770	0.083*
O2	0.26239 (14)	0.38043 (11)	0.4552 (3)	0.0561 (4)
O3	0.18042 (15)	0.15245 (13)	1.2939 (3)	0.0660 (5)
O4	0.02356 (14)	0.11544 (12)	1.4512 (3)	0.0572 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0391 (10)	0.0391 (12)	0.0450 (11)	0.0002 (8)	0.0049 (9)	−0.0029 (10)
C2	0.0418 (10)	0.0435 (12)	0.0494 (12)	−0.0029 (8)	0.0099 (9)	−0.0048 (9)
C3	0.0525 (13)	0.0533 (14)	0.0481 (14)	−0.0039 (10)	0.0069 (10)	0.0079 (11)
C4	0.0442 (11)	0.0696 (17)	0.0587 (15)	0.0017 (10)	−0.0016 (10)	0.0162 (12)
C5	0.0377 (10)	0.0573 (15)	0.0632 (15)	0.0004 (10)	0.0066 (10)	0.0057 (11)
C6	0.0419 (10)	0.0420 (12)	0.0477 (12)	−0.0026 (9)	0.0087 (8)	−0.0025 (9)
C7	0.0417 (11)	0.0477 (14)	0.0526 (13)	−0.0010 (9)	0.0114 (10)	−0.0009 (10)
C8	0.0430 (12)	0.0476 (13)	0.0466 (12)	−0.0036 (9)	0.0130 (9)	−0.0022 (10)
C9	0.0701 (16)	0.0767 (18)	0.0617 (17)	0.0157 (14)	0.0148 (13)	0.0164 (14)
C10	0.0583 (15)	0.098 (2)	0.081 (2)	−0.0028 (14)	0.0332 (14)	0.0230 (16)
N1	0.0457 (9)	0.0486 (11)	0.0459 (9)	−0.0044 (8)	0.0120 (8)	0.0006 (9)
N2	0.0388 (9)	0.0593 (12)	0.0544 (12)	−0.0024 (8)	0.0135 (8)	0.0107 (9)
O1	0.0429 (8)	0.0631 (10)	0.0591 (10)	0.0033 (8)	0.0050 (7)	0.0137 (8)
O2	0.0433 (8)	0.0628 (9)	0.0653 (10)	0.0004 (7)	0.0185 (7)	0.0103 (8)
O3	0.0413 (9)	0.0889 (13)	0.0689 (11)	0.0005 (8)	0.0122 (7)	0.0093 (10)
O4	0.0499 (8)	0.0641 (11)	0.0596 (10)	0.0070 (7)	0.0151 (7)	0.0183 (8)

C1—O1	1.361 (2)	C8—O3	1.192 (3)
C1—C6	1.399 (3)	C8—O4	1.347 (3)
C1—C2	1.404 (3)	C8—N2	1.349 (3)
C2—O2	1.367 (3)	C9—O4	1.438 (3)
C2—C3	1.382 (3)	C9—H9A	0.96
C3—C4	1.392 (3)	C9—H9B	0.96
C3—H3	0.93	C9—H9C	0.96
C4—C5	1.363 (4)	C10—O2	1.423 (3)
C4—H4	0.93	C10—H10A	0.96
C5—C6	1.405 (3)	C10—H10B	0.96
C5—H5	0.93	C10—H10C	0.96
C6—C7	1.460 (3)	N1—N2	1.374 (2)
C7—N1	1.277 (3)	N2—H2	0.86
C7—H7	0.93	O1—H1	0.82
O1—C1—C6	123.41 (19)	O3—C8—N2	125.9 (2)
O1—C1—C2	116.80 (17)	O4—C8—N2	109.70 (18)
C6—C1—C2	119.79 (19)	O4—C9—H9A	109.5
O2—C2—C3	125.2 (2)	O4—C9—H9B	109.5
O2—C2—C1	114.75 (19)	H9A—C9—H9B	109.5
C3—C2—C1	120.00 (19)	O4—C9—H9C	109.5
C2—C3—C4	119.8 (2)	H9A—C9—H9C	109.5
C2—C3—H3	120.1	H9B—C9—H9C	109.5
C4—C3—H3	120.1	O2—C10—H10A	109.5
C5—C4—C3	120.9 (2)	O2—C10—H10B	109.5
C5—C4—H4	119.6	H10A—C10—H10B	109.5
C3—C4—H4	119.6	O2—C10—H10C	109.5
C4—C5—C6	120.5 (2)	H10A—C10—H10C	109.5
C4—C5—H5	119.8	H10B—C10—H10C	109.5
C6—C5—H5	119.8	C7—N1—N2	118.03 (16)
C1—C6—C5	119.0 (2)	C8—N2—N1	117.36 (17)
C1—C6—C7	122.28 (19)	C8—N2—H2	121.3
C5—C6—C7	118.7 (2)	N1—N2—H2	121.3
N1—C7—C6	120.31 (18)	C1—O1—H1	109.5
N1—C7—H7	119.8	C2—O2—C10	116.9 (2)
C6—C7—H7	119.8	C8—O4—C9	114.74 (19)
O3—C8—O4	124.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.93	2.645 (2)	145
N2—H2···O2i	0.86	2.42	3.022 (2)	127
C5—H5···O3ii	0.93	2.49	3.320 (2)	149
C7—H7···O3ii	0.93	2.45	3.291 (2)	150
C3—H3···Cg1iii	0.93	2.85	3.606 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.93	2.645 (2)	145
N2—H2⋯O2i	0.86	2.42	3.022 (2)	127
C5—H5⋯O3ii	0.93	2.49	3.320 (2)	149
C7—H7⋯O3ii	0.93	2.45	3.291 (2)	150
C3—H3⋯Cg1iii	0.93	2.85	3.606 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.