(E)-Methyl N'-(4-hydroxy-benzyl-idene)hydrazinecarboxyl-ate.

In the title compound, C(9)H(10)N(2)O(3), the hydroxy group and the C=N-N unit are coplanar with the benzene ring. The benzene rings of inversion-related mol-ecules are stacked with their centroids separated by a distance of 3.7703 (9) Å, indicating weak π-π inter-actions. In the crystal structure, C-H⋯O, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link molecules into a infinite two-dimensional network along the a axis.

Related literature

For general background, see: Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶); Parashar et al. (2005). For a related structure, see: Shang et al. (2007 ▶). For related literature, see: Parashar et al. (1988 ▶).

Experimental

Crystal data

C9H10N2O3

M = 194.19

Monoclinic,

a = 8.1943 (8) Å

b = 12.0512 (11) Å

c = 10.1067 (9) Å

β = 111.970 (3)°

V = 925.57 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 123 (2) K

0.31 × 0.28 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.969, T max = 0.978

9552 measured reflections

1623 independent reflections

1487 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.115

S = 0.95

1623 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 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/S1600536808018096/tk2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018096/tk2273Isup2.hkl

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

C9H10N2O3	F000 = 408
Mr = 194.19	Dx = 1.394 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1628 reflections
a = 8.1943 (8) Å	θ = 2.0–25.0º
b = 12.0512 (11) Å	µ = 0.11 mm−1
c = 10.1067 (9) Å	T = 123 (2) K
β = 111.970 (3)º	Block, colourless
V = 925.57 (15) Å3	0.31 × 0.28 × 0.24 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1623 independent reflections
Radiation source: fine-focus sealed tube	1487 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 123(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.969, Tmax = 0.978	k = −13→14
9552 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) + (0.0871P)2 + 0.1838P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 0.95	Δρmax = 0.24 e Å−3
1623 reflections	Δρmin = −0.19 e Å−3
128 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: 0.288 (19)
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
O1	0.38082 (14)	0.30936 (8)	0.37656 (11)	0.0529 (3)
H1	0.3162	0.3134	0.2897	0.079*
O2	0.97787 (14)	−0.29441 (9)	0.29627 (10)	0.0516 (3)
O3	1.11604 (14)	−0.37383 (8)	0.51277 (11)	0.0520 (3)
N2	0.94810 (15)	−0.22777 (9)	0.49593 (12)	0.0440 (3)
H2A	0.9787	−0.2353	0.5887	0.053*
N1	0.83415 (14)	−0.14299 (9)	0.42392 (11)	0.0395 (3)
C5	0.57987 (17)	0.04812 (11)	0.32350 (13)	0.0396 (4)
H5	0.5728	−0.0024	0.2494	0.047*
C6	0.69854 (16)	0.02765 (10)	0.46270 (13)	0.0369 (3)
C3	0.47278 (17)	0.14106 (11)	0.29260 (13)	0.0408 (4)
H3	0.3932	0.1538	0.1976	0.049*
C1	0.48094 (16)	0.21605 (10)	0.39995 (14)	0.0390 (4)
C2	0.59680 (18)	0.19579 (11)	0.53868 (14)	0.0428 (4)
H2	0.6028	0.2459	0.6129	0.051*
C4	0.70306 (17)	0.10317 (12)	0.56872 (14)	0.0410 (4)
H4	0.7815	0.0904	0.6641	0.049*
C8	1.01137 (16)	−0.29807 (11)	0.42353 (14)	0.0386 (4)
C7	0.81502 (16)	−0.06805 (11)	0.50677 (14)	0.0398 (4)
H7	0.8828	−0.0755	0.6058	0.048*
C9	1.1945 (2)	−0.45473 (13)	0.4509 (2)	0.0619 (5)
H9A	1.2675	−0.5054	0.5253	0.093*
H9B	1.2678	−0.4171	0.4071	0.093*
H9C	1.1018	−0.4969	0.3778	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0548 (6)	0.0432 (6)	0.0517 (6)	0.0084 (4)	0.0096 (5)	−0.0039 (4)
O2	0.0574 (6)	0.0589 (7)	0.0365 (6)	0.0024 (5)	0.0154 (5)	−0.0063 (4)
O3	0.0570 (6)	0.0504 (6)	0.0506 (6)	0.0140 (5)	0.0226 (5)	0.0073 (4)
N2	0.0520 (7)	0.0473 (7)	0.0344 (6)	0.0110 (5)	0.0181 (5)	0.0068 (5)
N1	0.0390 (6)	0.0411 (6)	0.0388 (6)	0.0018 (4)	0.0153 (5)	0.0040 (5)
C5	0.0446 (7)	0.0398 (7)	0.0358 (7)	−0.0025 (5)	0.0168 (5)	−0.0020 (5)
C6	0.0376 (6)	0.0367 (7)	0.0384 (7)	−0.0047 (5)	0.0164 (5)	0.0018 (5)
C3	0.0416 (7)	0.0423 (7)	0.0357 (7)	−0.0026 (5)	0.0111 (5)	0.0022 (5)
C1	0.0383 (7)	0.0340 (7)	0.0451 (8)	−0.0036 (5)	0.0161 (6)	0.0005 (5)
C2	0.0464 (7)	0.0408 (7)	0.0405 (7)	−0.0039 (6)	0.0155 (6)	−0.0063 (6)
C4	0.0421 (7)	0.0435 (8)	0.0352 (6)	−0.0041 (5)	0.0118 (5)	−0.0001 (5)
C8	0.0372 (7)	0.0407 (7)	0.0381 (7)	−0.0041 (5)	0.0141 (5)	−0.0006 (5)
C7	0.0419 (7)	0.0423 (8)	0.0351 (7)	−0.0020 (5)	0.0142 (5)	0.0020 (5)
C9	0.0611 (10)	0.0503 (9)	0.0785 (12)	0.0113 (7)	0.0311 (8)	−0.0005 (8)

O1—C1	1.3595 (16)	C6—C4	1.3958 (18)
O1—H1	0.8400	C6—C7	1.4565 (18)
O2—C8	1.2114 (17)	C3—C1	1.3943 (19)
O3—C8	1.3431 (16)	C3—H3	0.9500
O3—C9	1.4339 (18)	C1—C2	1.3895 (19)
N1—N2	1.3917 (15)	C2—C4	1.3778 (19)
N2—H2A	0.8800	C2—H2	0.9500
N1—C7	1.2805 (17)	C4—H4	0.9500
N2—C8	1.3438 (17)	C7—H7	0.9500
C5—C3	1.3846 (18)	C9—H9A	0.9800
C5—C6	1.4007 (18)	C9—H9B	0.9800
C5—H5	0.9500	C9—H9C	0.9800
C1—O1—H1	109.5	C4—C2—C1	120.11 (12)
C8—O3—C9	116.56 (12)	C4—C2—H2	119.9
N1—N2—C8	119.88 (11)	C1—C2—H2	119.9
C8—N2—H2A	120.1	C2—C4—C6	121.73 (12)
N1—N2—H2A	120.1	C2—C4—H4	119.1
N2—N1—C7	113.47 (11)	C6—C4—H4	119.1
C3—C5—C6	120.82 (12)	O2—C8—O3	124.88 (12)
C3—C5—H5	119.6	O2—C8—N2	125.09 (13)
C6—C5—H5	119.6	O3—C8—N2	110.03 (11)
C4—C6—C5	117.73 (12)	N1—C7—C6	125.81 (11)
C4—C6—C7	117.09 (11)	N1—C7—H7	117.1
C5—C6—C7	125.16 (12)	C6—C7—H7	117.1
C5—C3—C1	120.46 (12)	O3—C9—H9A	109.5
C5—C3—H3	119.8	O3—C9—H9B	109.5
C1—C3—H3	119.8	H9A—C9—H9B	109.5
O1—C1—C2	117.44 (12)	O3—C9—H9C	109.5
O1—C1—C3	123.41 (12)	H9A—C9—H9C	109.5
C2—C1—C3	119.14 (12)	H9B—C9—H9C	109.5
C8—N2—N1—C7	−165.18 (12)	C5—C6—C4—C2	−0.82 (19)
C3—C5—C6—C4	0.84 (18)	C7—C6—C4—C2	−179.27 (11)
C3—C5—C6—C7	179.14 (12)	C9—O3—C8—O2	0.9 (2)
C6—C5—C3—C1	−0.14 (19)	C9—O3—C8—N2	−179.72 (12)
C5—C3—C1—O1	179.33 (12)	N1—N2—C8—O2	0.3 (2)
C5—C3—C1—C2	−0.60 (19)	N1—N2—C8—O3	−179.11 (10)
O1—C1—C2—C4	−179.31 (12)	N2—N1—C7—C6	−177.08 (11)
C3—C1—C2—C4	0.62 (19)	C4—C6—C7—N1	−176.85 (12)
C1—C2—C4—C6	0.1 (2)	C5—C6—C7—N1	4.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	2.58	3.068 (2)	118
O1—H1···N1i	0.84	2.11	2.941 (2)	169
N2—H2A···O2ii	0.88	2.13	2.964 (2)	158
C7—H7···O2ii	0.95	2.38	3.188 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	2.58	3.068 (2)	118
O1—H1⋯N1i	0.84	2.11	2.941 (2)	169
N2—H2A⋯O2ii	0.88	2.13	2.964 (2)	158
C7—H7⋯O2ii	0.95	2.38	3.188 (2)	143

Symmetry codes: (i) ; (ii) .