Methyl 2-[(E)-3-hydr-oxy-4-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 bond. The hydrazinecarboxyl-ate group is twisted from the benzene ring by 6.62 (5)° and an intramolecular O-H⋯O hydrogen bond occurs. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (100) by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

Related literature

For properties of benzaldehyde­hydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For Schiff base n class="Chemical">metal complexes, 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 = 7.7223 (12) Å

b = 9.2106 (14) Å

c = 15.092 (2) Å

β = 100.944 (6)°

V = 1054.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 223 K

0.18 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.978, T max = 0.982

5767 measured reflections

1944 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.05

1944 reflections

149 parameters

H-atom parameters constrained

Δρmax = 0.19 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/S1600536809018996/ci2804sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018996/ci2804Isup2.hkl

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

C10H12N2O4	F(000) = 472
Mr = 224.22	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1944 reflections
a = 7.7223 (12) Å	θ = 2.6–25.5°
b = 9.2106 (14) Å	µ = 0.11 mm−1
c = 15.092 (2) Å	T = 223 K
β = 100.944 (6)°	Block, colourless
V = 1054.0 (3) Å3	0.18 × 0.16 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1944 independent reflections
Radiation source: fine-focus sealed tube	1657 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
Tmin = 0.978, Tmax = 0.982	k = −11→11
5767 measured reflections	l = −18→18

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.1597P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1944 reflections	Δρmax = 0.19 e Å−3
149 parameters	Δρmin = −0.18 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: 0.035 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C9	1.14900 (17)	0.19752 (13)	0.79259 (8)	0.0395 (3)
C8	0.89788 (18)	0.11117 (13)	0.58309 (9)	0.0435 (3)
H8	0.8814	0.0133	0.5941	0.052*
C3	0.78128 (16)	0.37223 (13)	0.39017 (8)	0.0386 (3)
C5	0.84592 (17)	0.31881 (13)	0.47483 (8)	0.0392 (3)
H5	0.9053	0.3802	0.5193	0.047*
C7	0.82305 (17)	0.17208 (13)	0.49464 (8)	0.0399 (3)
C2	0.68958 (16)	0.28075 (14)	0.32243 (8)	0.0401 (3)
C6	0.73162 (19)	0.08300 (14)	0.42746 (9)	0.0475 (3)
H6	0.7149	−0.0143	0.4401	0.057*
C4	0.66479 (18)	0.13636 (14)	0.34190 (9)	0.0466 (3)
H4	0.6035	0.0753	0.2978	0.056*
C10	1.3093 (2)	0.17575 (17)	0.94154 (9)	0.0564 (4)
H10A	1.3936	0.2432	0.9261	0.085*
H10B	1.3697	0.1025	0.9810	0.085*
H10C	1.2281	0.2263	0.9714	0.085*
C1	0.5523 (2)	0.25850 (18)	0.16765 (10)	0.0575 (4)
H1A	0.6295	0.1791	0.1614	0.086*
H1B	0.5317	0.3150	0.1132	0.086*
H1C	0.4422	0.2214	0.1787	0.086*
O1	0.63158 (13)	0.34761 (10)	0.24138 (6)	0.0500 (3)
O4	1.21426 (13)	0.10865 (10)	0.86081 (6)	0.0513 (3)
O3	1.17310 (14)	0.32803 (9)	0.79258 (6)	0.0529 (3)
O2	0.80571 (14)	0.51620 (9)	0.37432 (6)	0.0520 (3)
H2	0.7894	0.5307	0.3197	0.078*
N1	0.98497 (14)	0.18969 (11)	0.64511 (7)	0.0420 (3)
N2	1.05406 (15)	0.12010 (11)	0.72457 (7)	0.0442 (3)
H2A	1.0369	0.0287	0.7307	0.053*

	U11	U22	U33	U12	U13	U23
C9	0.0475 (7)	0.0337 (6)	0.0380 (7)	0.0026 (5)	0.0096 (5)	0.0032 (5)
C8	0.0531 (8)	0.0325 (6)	0.0440 (7)	−0.0037 (5)	0.0067 (6)	0.0023 (5)
C3	0.0427 (7)	0.0331 (6)	0.0406 (7)	0.0000 (5)	0.0091 (5)	−0.0006 (5)
C5	0.0441 (7)	0.0354 (6)	0.0372 (6)	−0.0039 (5)	0.0057 (5)	−0.0032 (5)
C7	0.0425 (7)	0.0369 (6)	0.0397 (7)	−0.0015 (5)	0.0067 (5)	0.0002 (5)
C2	0.0412 (7)	0.0415 (7)	0.0369 (7)	0.0025 (5)	0.0060 (5)	−0.0007 (5)
C6	0.0571 (8)	0.0335 (6)	0.0497 (8)	−0.0070 (6)	0.0045 (6)	−0.0007 (5)
C4	0.0518 (8)	0.0417 (7)	0.0430 (7)	−0.0061 (6)	0.0003 (6)	−0.0079 (5)
C10	0.0626 (9)	0.0631 (9)	0.0391 (8)	−0.0074 (7)	−0.0015 (6)	0.0067 (6)
C1	0.0618 (9)	0.0646 (9)	0.0411 (8)	−0.0054 (7)	−0.0030 (6)	−0.0032 (7)
O1	0.0606 (6)	0.0474 (5)	0.0377 (5)	0.0009 (4)	−0.0018 (4)	0.0008 (4)
O4	0.0664 (6)	0.0407 (5)	0.0416 (5)	−0.0009 (4)	−0.0027 (4)	0.0066 (4)
O3	0.0776 (7)	0.0341 (5)	0.0440 (5)	−0.0049 (4)	0.0038 (5)	0.0007 (4)
O2	0.0772 (7)	0.0348 (5)	0.0415 (5)	−0.0048 (4)	0.0053 (5)	0.0044 (4)
N1	0.0517 (6)	0.0348 (5)	0.0380 (6)	0.0009 (4)	0.0049 (5)	0.0046 (4)
N2	0.0602 (7)	0.0300 (5)	0.0393 (6)	−0.0015 (5)	0.0015 (5)	0.0040 (4)

C9—O3	1.2164 (15)	C6—C4	1.3864 (19)
C9—O4	1.3369 (15)	C6—H6	0.93
C9—N2	1.3469 (16)	C4—H4	0.93
C8—N1	1.2698 (16)	C10—O4	1.4371 (16)
C8—C7	1.4621 (17)	C10—H10A	0.96
C8—H8	0.93	C10—H10B	0.96
C3—O2	1.3669 (14)	C10—H10C	0.96
C3—C5	1.3717 (17)	C1—O1	1.4241 (16)
C3—C2	1.4078 (17)	C1—H1A	0.96
C5—C7	1.4025 (17)	C1—H1B	0.96
C5—H5	0.93	C1—H1C	0.96
C7—C6	1.3885 (18)	O2—H2	0.82
C2—O1	1.3668 (15)	N1—N2	1.3750 (14)
C2—C4	1.3831 (19)	N2—H2A	0.86
O3—C9—O4	124.74 (12)	C2—C4—H4	120.1
O3—C9—N2	125.75 (11)	C6—C4—H4	120.1
O4—C9—N2	109.51 (10)	O4—C10—H10A	109.5
N1—C8—C7	121.11 (11)	O4—C10—H10B	109.5
N1—C8—H8	119.4	H10A—C10—H10B	109.5
C7—C8—H8	119.4	O4—C10—H10C	109.5
O2—C3—C5	118.24 (11)	H10A—C10—H10C	109.5
O2—C3—C2	121.38 (11)	H10B—C10—H10C	109.5
C5—C3—C2	120.37 (11)	O1—C1—H1A	109.5
C3—C5—C7	120.40 (11)	O1—C1—H1B	109.5
C3—C5—H5	119.8	H1A—C1—H1B	109.5
C7—C5—H5	119.8	O1—C1—H1C	109.5
C6—C7—C5	118.74 (12)	H1A—C1—H1C	109.5
C6—C7—C8	119.87 (11)	H1B—C1—H1C	109.5
C5—C7—C8	121.36 (11)	C2—O1—C1	117.31 (11)
O1—C2—C4	126.04 (11)	C9—O4—C10	116.53 (10)
O1—C2—C3	114.48 (11)	C3—O2—H2	109.5
C4—C2—C3	119.47 (11)	C8—N1—N2	116.16 (10)
C4—C6—C7	121.22 (12)	C9—N2—N1	118.88 (10)
C4—C6—H6	119.4	C9—N2—H2A	120.6
C7—C6—H6	119.4	N1—N2—H2A	120.6
C2—C4—C6	119.79 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.28	2.6871 (13)	112
O2—H2···O3i	0.82	2.20	2.9303 (13)	148
N2—H2A···O3ii	0.86	2.44	3.1951 (15)	147
C8—H8···O3ii	0.93	2.51	3.3185 (16)	146
C10—H10A···Cg1iii	0.96	2.87	3.6878 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	2.28	2.6871 (13)	112
O2—H2⋯O3i	0.82	2.20	2.9303 (13)	148
N2—H2A⋯O3ii	0.86	2.44	3.1951 (15)	147
C8—H8⋯O3ii	0.93	2.51	3.3185 (16)	146
C10—H10A⋯Cg1iii	0.96	2.87	3.6878 (18)	143

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C2–C7 ring.