Methyl (E)-N'-[1-(2,4-dihydroxy-phen-yl)ethyl-idene]hydrazinecarboxyl-ate.

The mol-ecule of the title compound, C(10)H(12)N(2)O(4), adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the methyl hydrazinecarboxyl-ate plane is 3.01 (6)°. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal, mol-ecules are linked into a two-dimensional network parallel to (10) by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds.

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 a related structure, see: Lv et al. (2008 ▶).

Experimental

Crystal data

C10H12N2O4

M = 224.22

Monoclinic,

a = 10.714 (5) Å

b = 8.700 (4) Å

c = 11.682 (6) Å

β = 107.872 (6)°

V = 1036.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 223 K

0.24 × 0.23 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2002 ▶) T min = 0.977, T max = 0.980

5096 measured reflections

1815 independent reflections

1355 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.05

1815 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 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/S1600536809027317/ci2854sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027317/ci2854Isup2.hkl

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

C10H12N2O4	F(000) = 472
Mr = 224.22	Dx = 1.437 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1915 reflections
a = 10.714 (5) Å	θ = 2.3–25.0°
b = 8.700 (4) Å	µ = 0.11 mm−1
c = 11.682 (6) Å	T = 223 K
β = 107.872 (6)°	Block, colourless
V = 1036.3 (9) Å3	0.24 × 0.23 × 0.19 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1815 independent reflections
Radiation source: fine-focus sealed tube	1355 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS, Bruker, 2002)	h = −12→12
Tmin = 0.977, Tmax = 0.980	k = −10→10
5096 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.2997P] where P = (Fo2 + 2Fc2)/3
1815 reflections	(Δ/σ)max = 0.025
149 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.18 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
O4	0.75341 (14)	0.02754 (18)	0.04159 (13)	0.0531 (4)
O2	0.30274 (15)	0.34157 (19)	−0.17412 (12)	0.0549 (5)
H2	0.3710	0.2990	−0.1355	0.082*
O1	−0.00973 (15)	0.70770 (19)	−0.13812 (14)	0.0615 (5)
H1	−0.0390	0.6873	−0.2100	0.092*
O3	0.59381 (15)	0.1012 (2)	−0.12508 (13)	0.0592 (5)
C6	0.32217 (19)	0.4395 (2)	0.02586 (17)	0.0403 (5)
C7	0.44242 (19)	0.3525 (2)	0.08526 (18)	0.0426 (5)
C2	0.1513 (2)	0.5234 (2)	−0.15377 (18)	0.0461 (5)
H2A	0.1139	0.5203	−0.2369	0.055*
C9	0.64512 (19)	0.1050 (2)	−0.01725 (18)	0.0443 (5)
C1	0.26013 (19)	0.4342 (2)	−0.09982 (17)	0.0404 (5)
C3	0.0972 (2)	0.6171 (2)	−0.08632 (19)	0.0458 (5)
C5	0.2630 (2)	0.5360 (3)	0.09052 (19)	0.0501 (6)
H5	0.3002	0.5422	0.1735	0.060*
C4	0.1528 (2)	0.6219 (3)	0.03705 (19)	0.0522 (6)
H4	0.1160	0.6829	0.0836	0.063*
C10	0.8151 (2)	−0.0586 (3)	−0.0320 (2)	0.0615 (7)
H10A	0.7509	−0.1217	−0.0874	0.092*
H10B	0.8830	−0.1225	0.0184	0.092*
H10C	0.8526	0.0113	−0.0760	0.092*
C8	0.5058 (2)	0.3622 (3)	0.21894 (19)	0.0646 (7)
H8A	0.5988	0.3485	0.2374	0.097*
H8B	0.4708	0.2833	0.2577	0.097*
H8C	0.4882	0.4611	0.2471	0.097*
N2	0.60110 (16)	0.1850 (2)	0.06181 (15)	0.0469 (5)
H2B	0.6418	0.1831	0.1377	0.056*
N1	0.48811 (16)	0.2697 (2)	0.01548 (15)	0.0448 (5)

	U11	U22	U33	U12	U13	U23
O4	0.0468 (9)	0.0614 (10)	0.0448 (9)	0.0087 (7)	0.0047 (7)	0.0031 (7)
O2	0.0550 (9)	0.0643 (11)	0.0377 (8)	0.0175 (8)	0.0030 (7)	−0.0073 (7)
O1	0.0555 (10)	0.0627 (11)	0.0593 (10)	0.0148 (8)	0.0072 (8)	−0.0074 (8)
O3	0.0557 (9)	0.0700 (11)	0.0409 (9)	−0.0038 (8)	−0.0012 (7)	−0.0013 (8)
C6	0.0421 (11)	0.0408 (12)	0.0367 (11)	−0.0074 (9)	0.0102 (9)	0.0013 (9)
C7	0.0427 (11)	0.0445 (12)	0.0380 (11)	−0.0073 (9)	0.0084 (9)	0.0079 (9)
C2	0.0478 (12)	0.0482 (13)	0.0362 (11)	0.0001 (10)	0.0041 (9)	−0.0042 (9)
C9	0.0403 (11)	0.0470 (13)	0.0401 (12)	−0.0083 (10)	0.0044 (9)	0.0045 (10)
C1	0.0432 (11)	0.0401 (12)	0.0361 (11)	−0.0026 (9)	0.0096 (9)	−0.0024 (9)
C3	0.0423 (11)	0.0439 (12)	0.0489 (12)	−0.0008 (9)	0.0107 (10)	−0.0023 (10)
C5	0.0568 (13)	0.0568 (14)	0.0357 (11)	−0.0069 (11)	0.0127 (10)	−0.0018 (10)
C4	0.0574 (13)	0.0538 (14)	0.0482 (13)	0.0002 (11)	0.0202 (11)	−0.0081 (11)
C10	0.0548 (14)	0.0669 (16)	0.0635 (16)	0.0034 (12)	0.0191 (12)	−0.0028 (13)
C8	0.0664 (15)	0.0796 (18)	0.0404 (13)	0.0092 (13)	0.0053 (11)	0.0068 (12)
N2	0.0413 (10)	0.0562 (11)	0.0370 (9)	0.0021 (8)	0.0031 (8)	0.0065 (8)
N1	0.0377 (9)	0.0485 (11)	0.0435 (10)	−0.0013 (8)	0.0055 (7)	0.0078 (8)

O4—C9	1.335 (2)	C2—H2A	0.93
O4—C10	1.445 (3)	C9—N2	1.352 (3)
O2—C1	1.362 (2)	C3—C4	1.381 (3)
O2—H2	0.82	C5—C4	1.375 (3)
O1—C3	1.369 (2)	C5—H5	0.93
O1—H1	0.82	C4—H4	0.93
O3—C9	1.210 (2)	C10—H10A	0.96
C6—C5	1.404 (3)	C10—H10B	0.96
C6—C1	1.414 (3)	C10—H10C	0.96
C6—C7	1.472 (3)	C8—H8A	0.96
C7—N1	1.291 (3)	C8—H8B	0.96
C7—C8	1.502 (3)	C8—H8C	0.96
C2—C3	1.378 (3)	N2—N1	1.378 (2)
C2—C1	1.381 (3)	N2—H2B	0.86
C9—O4—C10	116.06 (17)	C4—C5—H5	118.4
C1—O2—H2	109.5	C6—C5—H5	118.4
C3—O1—H1	109.5	C5—C4—C3	119.5 (2)
C5—C6—C1	115.61 (19)	C5—C4—H4	120.2
C5—C6—C7	121.90 (19)	C3—C4—H4	120.2
C1—C6—C7	122.48 (19)	O4—C10—H10A	109.5
N1—C7—C6	115.85 (18)	O4—C10—H10B	109.5
N1—C7—C8	123.37 (19)	H10A—C10—H10B	109.5
C6—C7—C8	120.8 (2)	O4—C10—H10C	109.5
C3—C2—C1	121.02 (19)	H10A—C10—H10C	109.5
C3—C2—H2A	119.5	H10B—C10—H10C	109.5
C1—C2—H2A	119.5	C7—C8—H8A	109.5
O3—C9—O4	124.6 (2)	C7—C8—H8B	109.5
O3—C9—N2	125.6 (2)	H8A—C8—H8B	109.5
O4—C9—N2	109.78 (17)	C7—C8—H8C	109.5
O2—C1—C2	116.30 (17)	H8A—C8—H8C	109.5
O2—C1—C6	122.56 (18)	H8B—C8—H8C	109.5
C2—C1—C6	121.14 (19)	C9—N2—N1	117.11 (17)
O1—C3—C2	121.94 (19)	C9—N2—H2B	121.4
O1—C3—C4	118.56 (19)	N1—N2—H2B	121.4
C2—C3—C4	119.5 (2)	C7—N1—N2	120.52 (17)
C4—C5—C6	123.2 (2)
C5—C6—C7—N1	−178.96 (18)	C1—C2—C3—O1	179.24 (19)
C1—C6—C7—N1	−0.3 (3)	C1—C2—C3—C4	0.1 (3)
C5—C6—C7—C8	0.9 (3)	C1—C6—C5—C4	−0.6 (3)
C1—C6—C7—C8	179.6 (2)	C7—C6—C5—C4	178.17 (19)
C10—O4—C9—O3	3.7 (3)	C6—C5—C4—C3	−1.2 (3)
C10—O4—C9—N2	−177.44 (17)	O1—C3—C4—C5	−177.7 (2)
C3—C2—C1—O2	177.60 (19)	C2—C3—C4—C5	1.5 (3)
C3—C2—C1—C6	−2.0 (3)	O3—C9—N2—N1	−0.1 (3)
C5—C6—C1—O2	−177.40 (18)	O4—C9—N2—N1	−178.99 (16)
C7—C6—C1—O2	3.8 (3)	C6—C7—N1—N2	179.30 (16)
C5—C6—C1—C2	2.2 (3)	C8—C7—N1—N2	−0.5 (3)
C7—C6—C1—C2	−176.56 (19)	C9—N2—N1—C7	−178.00 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.84	2.557 (2)	145
O1—H1···O3i	0.82	1.98	2.791 (2)	170
N2—H2B···O2ii	0.86	2.35	3.185 (2)	164
C2—H2A···O3i	0.93	2.42	3.141 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.84	2.557 (2)	145
O1—H1⋯O3i	0.82	1.98	2.791 (2)	170
N2—H2B⋯O2ii	0.86	2.35	3.185 (2)	164
C2—H2A⋯O3i	0.93	2.42	3.141 (3)	135

Symmetry codes: (i) ; (ii) .