Methyl N'-[(E)-4-hydr-oxy-3-methoxy-benzyl-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 double bond. The dihedral angle between the benzene ring and the hydrazinecarboxyl-ate mean plane is 36.54 (6)°. The mol-ecules are linked into a two-dimensional network by inter-molecular O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds, and by aromatic π-π stacking inter-actions [ring-centroid separation 3.7689 (9) Å].

Related literature

For a related structure, see: Cheng (2008 ▶).

Experimental

Crystal data

C10H12N2O4

M = 224.22

Monoclinic,

a = 9.4718 (10) Å

b = 11.0983 (11) Å

c = 10.3220 (11) Å

β = 98.272 (4)°

V = 1073.77 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 123 (2) K

0.29 × 0.27 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.965, T max = 0.968

11214 measured reflections

1887 independent reflections

1590 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.113

S = 1.02

1887 reflections

146 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/S1600536808019788/hb2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019788/hb2754Isup2.hkl

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

C10H12N2O4	F000 = 472
Mr = 224.22	Dx = 1.387 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1887 reflections
a = 9.4718 (10) Å	θ = 2.2–25.0º
b = 11.0983 (11) Å	µ = 0.11 mm−1
c = 10.3220 (11) Å	T = 123 (2) K
β = 98.272 (4)º	Block, colourless
V = 1073.77 (19) Å3	0.29 × 0.27 × 0.26 mm
Z = 4

Bruker SMART CCD diffractometer	1887 independent reflections
Radiation source: fine-focus sealed tube	1590 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 123(2) K	θmax = 25.0º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −11→10
Tmin = 0.965, Tmax = 0.968	k = −13→13
11214 measured reflections	l = −11→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1817P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.010
S = 1.02	Δρmax = 0.19 e Å−3
1887 reflections	Δρmin = −0.13 e Å−3
146 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: 0.036 (5)
Secondary atom site location: difference Fourier map

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
C1	0.46841 (16)	0.22471 (12)	0.90488 (15)	0.0408 (4)
C2	0.57541 (17)	0.23855 (13)	1.00956 (16)	0.0453 (4)
H2A	0.5760	0.3073	1.0645	0.054*
C3	0.46883 (16)	0.12325 (13)	0.82397 (14)	0.0405 (4)
C4	0.3402 (2)	0.01177 (17)	0.64655 (17)	0.0596 (5)
H4A	0.2550	0.0191	0.5809	0.089*
H4B	0.3309	−0.0589	0.7016	0.089*
H4C	0.4246	0.0026	0.6025	0.089*
C5	0.57560 (15)	0.03861 (13)	0.84778 (14)	0.0406 (4)
H5	0.5761	−0.0291	0.7916	0.049*
C6	0.68260 (16)	0.15212 (14)	1.03504 (15)	0.0439 (4)
H6	0.7554	0.1618	1.1079	0.053*
C7	0.68361 (15)	0.05223 (13)	0.95482 (14)	0.0390 (4)
C8	0.79364 (16)	−0.04036 (13)	0.98484 (15)	0.0425 (4)
H8	0.8497	−0.0414	1.0689	0.051*
C9	0.96010 (15)	−0.28026 (12)	0.85416 (14)	0.0381 (4)
C10	1.0957 (2)	−0.45396 (18)	0.82782 (19)	0.0681 (6)
H10A	1.1524	−0.5152	0.8804	0.102*
H10B	1.1562	−0.4113	0.7734	0.102*
H10C	1.0166	−0.4929	0.7715	0.102*
N1	0.81595 (13)	−0.11952 (11)	0.90087 (12)	0.0409 (3)
N2	0.91622 (13)	−0.20662 (11)	0.94426 (12)	0.0434 (3)
H2B	0.9502	−0.2137	1.0279	0.052*
O1	0.36374 (12)	0.30938 (9)	0.88270 (11)	0.0543 (3)
H1	0.3060	0.2900	0.8164	0.081*
O2	0.35509 (13)	0.11728 (10)	0.72612 (11)	0.0571 (4)
O3	0.93369 (12)	−0.26695 (10)	0.73659 (10)	0.0508 (3)
O4	1.03976 (12)	−0.36926 (10)	0.91342 (10)	0.0520 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0423 (8)	0.0368 (7)	0.0437 (9)	0.0025 (6)	0.0071 (6)	0.0028 (6)
C2	0.0511 (9)	0.0373 (8)	0.0469 (9)	0.0004 (6)	0.0045 (7)	−0.0050 (6)
C3	0.0410 (8)	0.0445 (8)	0.0360 (8)	0.0010 (6)	0.0055 (6)	0.0012 (6)
C4	0.0648 (11)	0.0618 (10)	0.0485 (10)	0.0017 (9)	−0.0038 (8)	−0.0113 (8)
C5	0.0432 (8)	0.0401 (8)	0.0398 (8)	0.0016 (6)	0.0101 (6)	−0.0025 (6)
C6	0.0431 (8)	0.0458 (8)	0.0415 (9)	−0.0022 (7)	0.0018 (6)	0.0014 (6)
C7	0.0387 (8)	0.0403 (7)	0.0390 (8)	−0.0002 (6)	0.0095 (6)	0.0040 (6)
C8	0.0431 (8)	0.0455 (8)	0.0387 (8)	0.0030 (6)	0.0056 (6)	0.0025 (6)
C9	0.0352 (7)	0.0434 (8)	0.0349 (8)	−0.0014 (6)	0.0029 (6)	0.0006 (6)
C10	0.0767 (13)	0.0687 (12)	0.0567 (11)	0.0307 (10)	0.0019 (9)	−0.0149 (9)
N1	0.0393 (7)	0.0442 (7)	0.0393 (7)	0.0059 (5)	0.0064 (5)	0.0070 (5)
N2	0.0465 (7)	0.0500 (7)	0.0328 (7)	0.0132 (6)	0.0033 (5)	0.0023 (5)
O1	0.0565 (7)	0.0465 (6)	0.0559 (7)	0.0137 (5)	−0.0053 (5)	−0.0084 (5)
O2	0.0551 (7)	0.0610 (7)	0.0501 (7)	0.0157 (5)	−0.0093 (5)	−0.0147 (5)
O3	0.0589 (7)	0.0593 (7)	0.0336 (7)	0.0073 (5)	0.0046 (5)	0.0001 (5)
O4	0.0612 (7)	0.0534 (7)	0.0402 (6)	0.0199 (5)	0.0026 (5)	−0.0030 (5)

C1—O1	1.3613 (17)	C6—H6	0.9500
C1—C2	1.380 (2)	C7—C8	1.465 (2)
C1—C3	1.402 (2)	C8—N1	1.2729 (19)
C2—C6	1.394 (2)	C8—H8	0.9500
C2—H2A	0.9500	C9—O3	1.2123 (18)
C3—O2	1.3682 (18)	C9—O4	1.3366 (17)
C3—C5	1.376 (2)	C9—N2	1.3479 (19)
C4—O2	1.4256 (19)	C10—O4	1.4421 (19)
C4—H4A	0.9800	C10—H10A	0.9800
C4—H4B	0.9800	C10—H10B	0.9800
C4—H4C	0.9800	C10—H10C	0.9800
C5—C7	1.402 (2)	N1—N2	1.3837 (16)
C5—H5	0.9500	N2—H2B	0.8800
C6—C7	1.385 (2)	O1—H1	0.8400
O1—C1—C2	119.35 (13)	C6—C7—C8	120.08 (13)
O1—C1—C3	121.23 (13)	C5—C7—C8	120.50 (13)
C2—C1—C3	119.42 (13)	N1—C8—C7	121.53 (13)
C1—C2—C6	120.28 (14)	N1—C8—H8	119.2
C1—C2—H2A	119.9	C7—C8—H8	119.2
C6—C2—H2A	119.9	O3—C9—O4	124.73 (13)
O2—C3—C5	125.38 (13)	O3—C9—N2	125.25 (13)
O2—C3—C1	114.15 (13)	O4—C9—N2	110.01 (12)
C5—C3—C1	120.45 (13)	O4—C10—H10A	109.5
O2—C4—H4A	109.5	O4—C10—H10B	109.5
O2—C4—H4B	109.5	H10A—C10—H10B	109.5
H4A—C4—H4B	109.5	O4—C10—H10C	109.5
O2—C4—H4C	109.5	H10A—C10—H10C	109.5
H4A—C4—H4C	109.5	H10B—C10—H10C	109.5
H4B—C4—H4C	109.5	C8—N1—N2	115.80 (12)
C3—C5—C7	120.09 (13)	C9—N2—N1	117.75 (12)
C3—C5—H5	120.0	C9—N2—H2B	121.1
C7—C5—H5	120.0	N1—N2—H2B	121.1
C7—C6—C2	120.37 (14)	C1—O1—H1	109.5
C7—C6—H6	119.8	C3—O2—C4	117.85 (12)
C2—C6—H6	119.8	C9—O4—C10	115.75 (12)
C6—C7—C5	119.38 (13)
O1—C1—C2—C6	179.17 (14)	C3—C5—C7—C8	176.91 (13)
C3—C1—C2—C6	−0.3 (2)	C6—C7—C8—N1	−165.42 (14)
O1—C1—C3—O2	−1.5 (2)	C5—C7—C8—N1	16.9 (2)
C2—C1—C3—O2	177.96 (14)	C7—C8—N1—N2	−175.85 (12)
O1—C1—C3—C5	179.93 (14)	O3—C9—N2—N1	10.3 (2)
C2—C1—C3—C5	−0.6 (2)	O4—C9—N2—N1	−170.91 (11)
O2—C3—C5—C7	−177.24 (13)	C8—N1—N2—C9	−169.52 (13)
C1—C3—C5—C7	1.1 (2)	C5—C3—O2—C4	4.0 (2)
C1—C2—C6—C7	0.7 (2)	C1—C3—O2—C4	−174.49 (14)
C2—C6—C7—C5	−0.1 (2)	O3—C9—O4—C10	−0.3 (2)
C2—C6—C7—C8	−177.83 (13)	N2—C9—O4—C10	−179.09 (14)
C3—C5—C7—C6	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	2.21	2.6695 (15)	114
O1—H1···O3i	0.84	2.34	3.0286 (16)	139
O1—H1···N1i	0.84	2.57	3.2640 (17)	140
N2—H2B···O3ii	0.88	2.19	3.0124 (16)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	2.21	2.6695 (15)	114
O1—H1⋯O3i	0.84	2.34	3.0286 (16)	139
O1—H1⋯N1i	0.84	2.57	3.2640 (17)	140
N2—H2B⋯O3ii	0.88	2.19	3.0124 (16)	155

Symmetry codes: (i) ; (ii) .