Ethyl N'-[(E)-4-hydroxy-benzyl-idene]hydrazinecarboxyl-ate at 123 K.

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 14.6 (1)°. Mol-ecules are linked into a three-dimensional network by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, and by C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C10H12N2O3

M = 208.22

Orthorhombic,

a = 11.342 (3) Å

b = 7.6114 (17) Å

c = 24.986 (5) Å

V = 2157.0 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 123 (2) K

0.26 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

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

21084 measured reflections

1900 independent reflections

1521 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.125

S = 1.02

1900 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.21 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/S1600536808019818/ci2620sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019818/ci2620Isup2.hkl

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

C10H12N2O3	F000 = 880
Mr = 208.22	Dx = 1.282 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1900 reflections
a = 11.342 (3) Å	θ = 1.6–25.0º
b = 7.6114 (17) Å	µ = 0.10 mm−1
c = 24.986 (5) Å	T = 123 (2) K
V = 2157.0 (9) Å3	Block, colourless
Z = 8	0.26 × 0.25 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	1900 independent reflections
Radiation source: fine-focus sealed tube	1521 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 123(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −13→13
Tmin = 0.965, Tmax = 0.968	k = −8→9
21084 measured reflections	l = −28→29

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0722P)2 + 0.4536P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.21 e Å−3
1900 reflections	Δρmin = −0.18 e Å−3
137 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: 0.0110 (18)
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
O2	0.38975 (10)	0.12445 (15)	0.06297 (5)	0.0550 (4)
O1	0.10016 (11)	0.07264 (18)	0.38449 (5)	0.0662 (4)
H1	0.0396	0.1121	0.3978	0.099*
O3	0.31948 (13)	0.34186 (17)	0.01045 (5)	0.0708 (4)
N1	0.23119 (12)	0.22542 (18)	0.13972 (5)	0.0472 (4)
N2	0.23619 (13)	0.29838 (19)	0.08895 (5)	0.0533 (4)
H2A	0.1859	0.3769	0.0794	0.064*
C4	0.21890 (13)	0.1206 (2)	0.25066 (6)	0.0451 (4)
H4	0.2850	0.0839	0.2317	0.054*
C6	0.13472 (13)	0.2248 (2)	0.22515 (6)	0.0422 (4)
C1	0.10857 (14)	0.1271 (2)	0.33239 (6)	0.0459 (4)
C3	0.02413 (14)	0.2324 (2)	0.30815 (7)	0.0493 (4)
H3	−0.0410	0.2707	0.3275	0.059*
C7	0.14800 (14)	0.2813 (2)	0.16958 (7)	0.0471 (4)
H7	0.0940	0.3608	0.1555	0.056*
C2	0.20628 (14)	0.0712 (2)	0.30315 (6)	0.0481 (4)
H2	0.2629	0.0004	0.3192	0.058*
C5	0.03729 (14)	0.2800 (2)	0.25500 (7)	0.0491 (4)
H5	−0.0197	0.3501	0.2389	0.059*
C8	0.32053 (15)	0.2449 (2)	0.05487 (6)	0.0489 (4)
C9	0.3972 (3)	0.2864 (3)	−0.03288 (9)	0.1029 (9)
H9A	0.4749	0.2601	−0.0188	0.123*
H9B	0.3663	0.1809	−0.0495	0.123*
C10	0.4055 (3)	0.4246 (4)	−0.07193 (10)	0.1096 (10)
H10A	0.4564	0.3880	−0.1005	0.164*
H10B	0.4372	0.5282	−0.0554	0.164*
H10C	0.3285	0.4497	−0.0859	0.164*

	U11	U22	U33	U12	U13	U23
O2	0.0572 (7)	0.0535 (7)	0.0542 (7)	0.0039 (6)	0.0023 (5)	0.0014 (5)
O1	0.0693 (8)	0.0818 (9)	0.0475 (8)	0.0116 (7)	0.0088 (6)	0.0139 (6)
O3	0.1000 (10)	0.0651 (8)	0.0472 (7)	0.0138 (7)	0.0168 (7)	0.0131 (6)
N1	0.0533 (8)	0.0472 (8)	0.0412 (8)	0.0007 (6)	0.0011 (6)	0.0059 (6)
N2	0.0639 (9)	0.0534 (8)	0.0426 (8)	0.0116 (7)	0.0048 (7)	0.0112 (6)
C4	0.0428 (8)	0.0455 (9)	0.0469 (9)	0.0038 (7)	0.0050 (7)	−0.0010 (7)
C6	0.0431 (8)	0.0387 (8)	0.0447 (9)	−0.0018 (6)	−0.0001 (6)	0.0012 (6)
C1	0.0508 (9)	0.0447 (9)	0.0421 (9)	−0.0033 (7)	0.0001 (7)	0.0022 (7)
C3	0.0426 (8)	0.0528 (10)	0.0526 (10)	0.0030 (7)	0.0077 (7)	0.0009 (8)
C7	0.0495 (9)	0.0447 (9)	0.0471 (10)	0.0040 (7)	−0.0013 (7)	0.0053 (7)
C2	0.0484 (8)	0.0478 (9)	0.0483 (10)	0.0063 (7)	−0.0029 (7)	0.0024 (7)
C5	0.0437 (8)	0.0501 (9)	0.0534 (10)	0.0061 (7)	0.0001 (7)	0.0069 (7)
C8	0.0592 (10)	0.0455 (9)	0.0418 (9)	−0.0046 (8)	0.0000 (7)	0.0011 (7)
C9	0.155 (3)	0.0936 (18)	0.0598 (14)	0.0209 (17)	0.0467 (16)	0.0063 (12)
C10	0.107 (2)	0.155 (3)	0.0666 (15)	0.0021 (19)	0.0209 (13)	0.0293 (16)

O2—C8	1.224 (2)	C1—C3	1.388 (2)
O1—C1	1.3695 (19)	C1—C2	1.394 (2)
O1—H1	0.82	C3—C5	1.385 (2)
O3—C8	1.3329 (19)	C3—H3	0.93
O3—C9	1.458 (3)	C7—H7	0.93
N1—C7	1.276 (2)	C2—H2	0.93
N1—N2	1.3860 (18)	C5—H5	0.93
N2—C8	1.344 (2)	C9—C10	1.437 (3)
N2—H2A	0.86	C9—H9A	0.97
C4—C2	1.372 (2)	C9—H9B	0.97
C4—C6	1.395 (2)	C10—H10A	0.96
C4—H4	0.93	C10—H10B	0.96
C6—C5	1.398 (2)	C10—H10C	0.96
C6—C7	1.462 (2)
C1—O1—H1	109.5	C4—C2—C1	120.03 (14)
C8—O3—C9	116.92 (16)	C4—C2—H2	120.0
C7—N1—N2	115.58 (13)	C1—C2—H2	120.0
C8—N2—N1	119.19 (14)	C3—C5—C6	121.20 (15)
C8—N2—H2A	120.4	C3—C5—H5	119.4
N1—N2—H2A	120.4	C6—C5—H5	119.4
C2—C4—C6	121.41 (14)	O2—C8—O3	123.93 (15)
C2—C4—H4	119.3	O2—C8—N2	125.36 (15)
C6—C4—H4	119.3	O3—C8—N2	110.71 (15)
C4—C6—C5	117.91 (15)	C10—C9—O3	109.4 (2)
C4—C6—C7	122.06 (14)	C10—C9—H9A	109.8
C5—C6—C7	119.99 (14)	O3—C9—H9A	109.8
O1—C1—C3	122.78 (14)	C10—C9—H9B	109.8
O1—C1—C2	117.48 (14)	O3—C9—H9B	109.8
C3—C1—C2	119.74 (15)	H9A—C9—H9B	108.2
C5—C3—C1	119.70 (15)	C9—C10—H10A	109.5
C5—C3—H3	120.1	C9—C10—H10B	109.5
C1—C3—H3	120.1	H10A—C10—H10B	109.5
N1—C7—C6	122.24 (15)	C9—C10—H10C	109.5
N1—C7—H7	118.9	H10A—C10—H10C	109.5
C6—C7—H7	118.9	H10B—C10—H10C	109.5
C7—N1—N2—C8	−179.28 (15)	C3—C1—C2—C4	0.2 (2)
C2—C4—C6—C5	0.9 (2)	C1—C3—C5—C6	−0.3 (3)
C2—C4—C6—C7	178.80 (15)	C4—C6—C5—C3	−0.3 (2)
O1—C1—C3—C5	−178.91 (15)	C7—C6—C5—C3	−178.25 (15)
C2—C1—C3—C5	0.4 (2)	C9—O3—C8—O2	7.1 (3)
N2—N1—C7—C6	−176.50 (13)	C9—O3—C8—N2	−173.16 (19)
C4—C6—C7—N1	6.8 (3)	N1—N2—C8—O2	6.4 (3)
C5—C6—C7—N1	−175.38 (15)	N1—N2—C8—O3	−173.41 (14)
C6—C4—C2—C1	−0.9 (2)	C8—O3—C9—C10	−166.9 (2)
O1—C1—C2—C4	179.54 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.96	2.752 (2)	161
N2—H2A···O2ii	0.86	2.11	2.936 (2)	161
C9—H9B···O1iii	0.97	2.57	3.425 (3)	148
C2—H2···Cg1iv	0.93	2.97	3.636 (2)	130
C5—H5···Cg1v	0.93	2.77	3.613 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.96	2.752 (2)	161
N2—H2A⋯O2ii	0.86	2.11	2.936 (2)	161
C9—H9B⋯O1iii	0.97	2.57	3.425 (3)	148
C2—H2⋯Cg1iv	0.93	2.97	3.636 (2)	130
C5—H5⋯Cg1v	0.93	2.77	3.613 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .