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

The mol-ecule of the title compound, C(10)H(12)N(2)O(3), adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the hydrazinecarboxyl-ate plane is 8.98 (7)°. Intra-molecular O-H⋯N and C-H⋯N hydrogen bonds are observed. Mol-ecules are linked into chains along the c axis by N-H⋯O hydrogen bonds. In addition, C-H⋯π inter-actions are observed.

Related literature

For general background, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For a related structure, see: Cheng (2008 ▶).

Experimental

Crystal data

C10H12N2O3

M = 208.22

Monoclinic,

a = 8.6432 (8) Å

b = 12.6696 (11) Å

c = 9.9810 (9) Å

β = 109.837 (3)°

V = 1028.12 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.28 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.973, T max = 0.979

10601 measured reflections

1809 independent reflections

1587 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.107

S = 1.05

1809 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.12 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/S1600536808024434/ci2645sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024434/ci2645Isup2.hkl

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

C10H12N2O3	F000 = 440
Mr = 208.22	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1809 reflections
a = 8.6432 (8) Å	θ = 2.5–25.0º
b = 12.6696 (11) Å	µ = 0.10 mm−1
c = 9.9810 (9) Å	T = 273 (2) K
β = 109.837 (3)º	Block, colourless
V = 1028.12 (16) Å3	0.28 × 0.24 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1809 independent reflections
Radiation source: fine-focus sealed tube	1587 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 273(2) K	θmax = 25.1º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −10→9
Tmin = 0.973, Tmax = 0.979	k = −14→13
10601 measured reflections	l = −11→11

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) + (0.0557P)2 + 0.2233P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.26 e Å−3
1809 reflections	Δρmin = −0.12 e Å−3
140 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: 0.017 (3)
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	0.62350 (16)	−0.02927 (10)	0.76460 (14)	0.0409 (3)
C6	0.67306 (16)	−0.04195 (10)	0.91401 (14)	0.0403 (3)
C7	0.79166 (16)	0.03028 (10)	1.01395 (13)	0.0404 (3)
C9	1.01051 (17)	0.25416 (11)	0.97214 (14)	0.0430 (3)
C2	0.51172 (17)	−0.09885 (12)	0.67429 (16)	0.0497 (4)
H2	0.4799	−0.0896	0.5762	0.060*
C3	0.44767 (19)	−0.18132 (12)	0.72853 (18)	0.0577 (4)
H3	0.3740	−0.2279	0.6671	0.069*
C5	0.60373 (19)	−0.12639 (12)	0.96486 (17)	0.0538 (4)
H5	0.6335	−0.1365	1.0627	0.065*
C4	0.4927 (2)	−0.19499 (14)	0.87417 (19)	0.0623 (5)
H4	0.4484	−0.2502	0.9109	0.075*
C10	1.1944 (2)	0.39775 (14)	1.01329 (19)	0.0650 (5)
H10A	1.2220	0.3668	0.9365	0.098*
H10B	1.2933	0.4178	1.0883	0.098*
H10C	1.1272	0.4591	0.9794	0.098*
C8	0.8508 (2)	0.00907 (13)	1.17083 (15)	0.0595 (4)
H8A	0.9553	0.0427	1.2149	0.089*
H8B	0.8622	−0.0657	1.1871	0.089*
H8C	0.7727	0.0365	1.2110	0.089*
O1	0.68111 (13)	0.04936 (8)	0.70165 (10)	0.0535 (3)
H1	0.7464	0.0857	0.7631	0.080*
O2	0.98628 (13)	0.25492 (8)	0.84561 (10)	0.0539 (3)
O3	1.10557 (14)	0.32236 (9)	1.06669 (11)	0.0603 (3)
N1	0.83941 (13)	0.10946 (9)	0.95665 (11)	0.0416 (3)
N2	0.94739 (14)	0.18236 (10)	1.04034 (11)	0.0470 (3)
H2A	0.9736	0.1824	1.1315	0.056*

	U11	U22	U33	U12	U13	U23
C1	0.0454 (7)	0.0377 (7)	0.0412 (7)	0.0050 (5)	0.0167 (6)	0.0020 (5)
C6	0.0439 (7)	0.0363 (7)	0.0421 (7)	0.0051 (5)	0.0167 (6)	0.0023 (5)
C7	0.0460 (7)	0.0404 (7)	0.0361 (7)	0.0071 (6)	0.0156 (6)	0.0029 (5)
C9	0.0477 (8)	0.0444 (8)	0.0381 (7)	−0.0012 (6)	0.0163 (6)	−0.0035 (6)
C2	0.0521 (8)	0.0504 (9)	0.0447 (8)	0.0007 (6)	0.0138 (6)	−0.0056 (6)
C3	0.0532 (9)	0.0511 (9)	0.0655 (10)	−0.0078 (7)	0.0156 (8)	−0.0084 (7)
C5	0.0632 (9)	0.0506 (9)	0.0495 (8)	−0.0015 (7)	0.0216 (7)	0.0089 (7)
C4	0.0659 (10)	0.0522 (9)	0.0710 (11)	−0.0131 (7)	0.0260 (8)	0.0056 (8)
C10	0.0688 (10)	0.0671 (11)	0.0637 (10)	−0.0237 (9)	0.0284 (8)	−0.0088 (8)
C8	0.0833 (11)	0.0526 (9)	0.0384 (8)	−0.0026 (8)	0.0151 (7)	0.0045 (7)
O1	0.0721 (7)	0.0501 (6)	0.0362 (5)	−0.0107 (5)	0.0155 (5)	0.0007 (4)
O2	0.0721 (7)	0.0544 (7)	0.0368 (6)	−0.0094 (5)	0.0206 (5)	−0.0010 (4)
O3	0.0716 (7)	0.0673 (7)	0.0464 (6)	−0.0274 (6)	0.0258 (5)	−0.0137 (5)
N1	0.0460 (6)	0.0423 (6)	0.0358 (6)	−0.0029 (5)	0.0130 (5)	−0.0021 (5)
N2	0.0563 (7)	0.0524 (7)	0.0319 (6)	−0.0097 (5)	0.0145 (5)	−0.0034 (5)

C1—O1	1.3592 (16)	C5—C4	1.381 (2)
C1—C2	1.390 (2)	C5—H5	0.93
C1—C6	1.4141 (19)	C4—H4	0.93
C6—C5	1.4027 (19)	C10—O3	1.4364 (19)
C6—C7	1.4796 (19)	C10—H10A	0.96
C7—N1	1.2899 (17)	C10—H10B	0.96
C7—C8	1.4974 (18)	C10—H10C	0.96
C9—O2	1.2081 (16)	C8—H8A	0.96
C9—O3	1.3364 (17)	C8—H8B	0.96
C9—N2	1.3567 (17)	C8—H8C	0.96
C2—C3	1.377 (2)	O1—H1	0.82
C2—H2	0.93	N1—N2	1.3757 (16)
C3—C4	1.382 (2)	N2—H2A	0.86
C3—H3	0.93
O1—C1—C2	116.62 (12)	C5—C4—C3	119.71 (15)
O1—C1—C6	122.91 (12)	C5—C4—H4	120.1
C2—C1—C6	120.46 (13)	C3—C4—H4	120.1
C5—C6—C1	117.03 (13)	O3—C10—H10A	109.5
C5—C6—C7	120.73 (12)	O3—C10—H10B	109.5
C1—C6—C7	122.23 (12)	H10A—C10—H10B	109.5
N1—C7—C6	115.77 (11)	O3—C10—H10C	109.5
N1—C7—C8	123.80 (13)	H10A—C10—H10C	109.5
C6—C7—C8	120.43 (12)	H10B—C10—H10C	109.5
O2—C9—O3	125.45 (13)	C7—C8—H8A	109.5
O2—C9—N2	124.98 (13)	C7—C8—H8B	109.5
O3—C9—N2	109.56 (11)	H8A—C8—H8B	109.5
C3—C2—C1	120.68 (14)	C7—C8—H8C	109.5
C3—C2—H2	119.7	H8A—C8—H8C	109.5
C1—C2—H2	119.7	H8B—C8—H8C	109.5
C2—C3—C4	120.09 (14)	C1—O1—H1	109.5
C2—C3—H3	120.0	C9—O3—C10	116.48 (11)
C4—C3—H3	120.0	C7—N1—N2	120.41 (11)
C4—C5—C6	122.01 (14)	C9—N2—N1	116.81 (11)
C4—C5—H5	119.0	C9—N2—H2A	121.6
C6—C5—H5	119.0	N1—N2—H2A	121.6
O1—C1—C6—C5	179.88 (12)	C1—C6—C5—C4	0.4 (2)
C2—C1—C6—C5	−0.42 (19)	C7—C6—C5—C4	179.96 (14)
O1—C1—C6—C7	0.3 (2)	C6—C5—C4—C3	0.2 (3)
C2—C1—C6—C7	−179.99 (12)	C2—C3—C4—C5	−0.8 (3)
C5—C6—C7—N1	−175.42 (12)	O2—C9—O3—C10	−4.6 (2)
C1—C6—C7—N1	4.12 (19)	N2—C9—O3—C10	174.30 (13)
C5—C6—C7—C8	5.3 (2)	C6—C7—N1—N2	178.87 (11)
C1—C6—C7—C8	−175.19 (13)	C8—C7—N1—N2	−1.8 (2)
O1—C1—C2—C3	179.57 (13)	O2—C9—N2—N1	−4.4 (2)
C6—C1—C2—C3	−0.2 (2)	O3—C9—N2—N1	176.72 (11)
C1—C2—C3—C4	0.8 (2)	C7—N1—N2—C9	170.54 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.5625 (14)	145
N2—H2A···O2i	0.86	2.25	3.0550 (14)	156
C8—H8A···N2	0.96	2.47	2.820 (2)	101
C8—H8C···Cg1ii	0.96	2.93	3.803 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.5625 (14)	145
N2—H2A⋯O2i	0.86	2.25	3.0550 (14)	156
C8—H8A⋯N2	0.96	2.47	2.820 (2)	101
C8—H8C⋯Cg1ii	0.96	2.93	3.803 (2)	151

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