(E)-Ethyl N'-(2-hydroxy-benzyl-idene)-hydrazinecarboxyl-ate.

There are two mol-ecules in the asymmetric unit of the title compound, C(10)H(12)N(2)O(3), with identical conformations. Each independent mol-ecule is approximately planar and adopts a trans configuration with respect to the C=N double bond. Intra-molecular O-H⋯N hydrogen bonds are observed in both mol-ecules. The mol-ecules are linked into a ribbon-like structure running along the b axis by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. The ribbons are arranged into layers parallel to (02).

Related literature

For the properties of benzaldehyde hydrazone derivatives, 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 = 208.12

Monoclinic,

a = 11.535 (11) Å

b = 22.05 (2) Å

c = 9.005 (9) Å

β = 111.669 (14)°

V = 2129 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.27 × 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 = 0.978

14192 measured reflections

3713 independent reflections

1445 reflections with I > 2σ(I)

R int = 0.146

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.150

S = 0.78

3713 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.16 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/S1600536808022307/ci2635sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022307/ci2635Isup2.hkl

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

C10H12N2O3	F000 = 880
Mr = 208.12	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3713 reflections
a = 11.535 (11) Å	θ = 1.9–25.0º
b = 22.05 (2) Å	µ = 0.10 mm−1
c = 9.005 (9) Å	T = 273 (2) K
β = 111.669 (14)º	Block, colourless
V = 2129 (4) Å3	0.27 × 0.24 × 0.23 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3713 independent reflections
Radiation source: fine-focus sealed tube	1445 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.146
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −13→12
Tmin = 0.973, Tmax = 0.978	k = −26→25
14192 measured reflections	l = −10→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058	w = 1/[σ2(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150	(Δ/σ)max = 0.001
S = 0.78	Δρmax = 0.30 e Å−3
3713 reflections	Δρmin = −0.16 e Å−3
274 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: 0.0017 (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
O1	0.6761 (2)	−0.00597 (8)	0.5564 (3)	0.1012 (8)
H1	0.6249	0.0071	0.4725	0.121*
O2	0.43571 (18)	−0.01273 (8)	0.1327 (2)	0.0799 (7)
O3	0.32487 (19)	0.06261 (8)	−0.0314 (2)	0.0781 (7)
N1	0.5648 (2)	0.07322 (10)	0.3410 (3)	0.0661 (7)
N2	0.4749 (2)	0.08742 (10)	0.1969 (3)	0.0740 (8)
H2A	0.4578	0.1246	0.1679	0.089*
C1	0.7458 (3)	0.04071 (13)	0.6420 (4)	0.0744 (10)
C2	0.8384 (3)	0.02856 (15)	0.7861 (4)	0.0988 (12)
H2	0.8519	−0.0121	0.8237	0.119*
C3	0.9126 (3)	0.07430 (16)	0.8778 (4)	0.1005 (12)
H3	0.9765	0.0650	0.9775	0.121*
C4	0.8937 (3)	0.13398 (15)	0.8240 (4)	0.0933 (11)
H4	0.9443	0.1658	0.8859	0.112*
C5	0.8007 (3)	0.14600 (14)	0.6797 (4)	0.0804 (10)
H5	0.7871	0.1868	0.6438	0.096*
C6	0.7250 (3)	0.10084 (12)	0.5834 (3)	0.0635 (8)
C7	0.6293 (3)	0.11571 (12)	0.4328 (3)	0.0669 (9)
H7A	0.6135	0.1569	0.4007	0.080*
C8	0.4133 (3)	0.04080 (14)	0.1007 (4)	0.0676 (9)
C9	0.2552 (3)	0.01839 (14)	−0.1492 (4)	0.0839 (11)
H9A	0.2072	−0.0083	−0.1044	0.101*
H9B	0.3129	−0.0071	−0.1809	0.101*
C10	0.1687 (3)	0.05187 (14)	−0.2907 (4)	0.0954 (11)
H10A	0.1209	0.0228	−0.3728	0.143*
H10B	0.2171	0.0783	−0.3338	0.143*
H10C	0.1113	0.0765	−0.2584	0.143*
O4	0.44788 (19)	0.28071 (8)	0.6198 (2)	0.0858 (7)
H4A	0.4920	0.2570	0.6873	0.103*
O5	0.7029 (2)	0.23103 (9)	0.9891 (3)	0.0972 (8)
O6	0.75313 (19)	0.14080 (8)	1.1180 (2)	0.0784 (7)
N3	0.5222 (2)	0.17646 (9)	0.7524 (3)	0.0661 (7)
N4	0.5985 (2)	0.14460 (10)	0.8822 (3)	0.0722 (8)
H6	0.5909	0.1061	0.8907	0.087*
C11	0.3641 (3)	0.24868 (13)	0.4965 (4)	0.0665 (9)
C12	0.2807 (3)	0.28054 (13)	0.3700 (4)	0.0814 (10)
H12	0.2822	0.3236	0.3710	0.098*
C13	0.1953 (3)	0.25032 (15)	0.2422 (4)	0.0898 (11)
H13	0.1383	0.2728	0.1561	0.108*
C14	0.1915 (3)	0.18688 (15)	0.2380 (4)	0.0929 (11)
H14	0.1337	0.1660	0.1492	0.111*
C15	0.2741 (3)	0.15531 (14)	0.3664 (4)	0.0786 (10)
H15	0.2715	0.1122	0.3647	0.094*
C16	0.3610 (3)	0.18441 (12)	0.4981 (3)	0.0623 (8)
C17	0.4436 (3)	0.14927 (13)	0.6327 (3)	0.0638 (8)
H17	0.4389	0.1063	0.6311	0.077*
C18	0.6864 (3)	0.17732 (15)	0.9965 (4)	0.0728 (9)
C19	0.8531 (3)	0.17077 (14)	1.2461 (4)	0.0906 (11)
H19A	0.8180	0.1976	1.3072	0.109*
H19B	0.9037	0.1958	1.2014	0.109*
C20	0.9322 (3)	0.12260 (14)	1.3527 (4)	0.1046 (12)
H20A	0.9974	0.1416	1.4441	0.157*
H20B	0.9710	0.0981	1.2928	0.157*
H20C	0.8802	0.0966	1.3909	0.157*

	U11	U22	U33	U12	U13	U23
O1	0.141 (2)	0.0421 (13)	0.0963 (17)	0.0008 (13)	0.0154 (15)	0.0104 (12)
O2	0.0980 (16)	0.0357 (11)	0.0895 (16)	0.0003 (11)	0.0154 (13)	0.0015 (10)
O3	0.0861 (15)	0.0492 (12)	0.0760 (15)	0.0038 (11)	0.0029 (13)	−0.0049 (11)
N1	0.0828 (18)	0.0437 (14)	0.0631 (17)	0.0054 (13)	0.0167 (15)	−0.0015 (12)
N2	0.0922 (19)	0.0389 (14)	0.0692 (18)	0.0031 (13)	0.0045 (16)	−0.0030 (13)
C1	0.097 (3)	0.049 (2)	0.070 (2)	0.0103 (18)	0.022 (2)	0.0070 (17)
C2	0.121 (3)	0.062 (2)	0.092 (3)	0.023 (2)	0.014 (3)	0.023 (2)
C3	0.103 (3)	0.093 (3)	0.078 (3)	0.023 (2)	0.001 (2)	0.012 (2)
C4	0.100 (3)	0.071 (2)	0.085 (3)	0.004 (2)	0.007 (2)	0.000 (2)
C5	0.092 (2)	0.0501 (19)	0.077 (2)	0.0031 (18)	0.005 (2)	0.0025 (17)
C6	0.073 (2)	0.0487 (18)	0.063 (2)	0.0105 (16)	0.0182 (18)	0.0068 (16)
C7	0.084 (2)	0.0419 (17)	0.065 (2)	0.0046 (16)	0.0151 (18)	−0.0006 (15)
C8	0.078 (2)	0.051 (2)	0.068 (2)	0.0029 (18)	0.0194 (19)	−0.0028 (17)
C9	0.090 (2)	0.062 (2)	0.081 (3)	−0.0088 (18)	0.009 (2)	−0.0169 (18)
C10	0.102 (3)	0.084 (2)	0.076 (2)	0.000 (2)	0.005 (2)	0.0031 (19)
O4	0.1091 (17)	0.0377 (11)	0.0897 (16)	−0.0034 (11)	0.0121 (14)	0.0022 (11)
O5	0.128 (2)	0.0383 (13)	0.0981 (17)	−0.0128 (12)	0.0095 (15)	−0.0045 (11)
O6	0.0879 (16)	0.0554 (13)	0.0721 (15)	−0.0046 (11)	0.0062 (13)	0.0023 (11)
N3	0.0805 (18)	0.0402 (14)	0.0678 (17)	0.0020 (13)	0.0159 (15)	0.0016 (13)
N4	0.0864 (19)	0.0336 (13)	0.0771 (18)	−0.0030 (13)	0.0075 (16)	0.0018 (13)
C11	0.081 (2)	0.0425 (18)	0.072 (2)	−0.0037 (16)	0.0228 (19)	−0.0017 (16)
C12	0.095 (3)	0.0512 (19)	0.089 (3)	0.0076 (19)	0.023 (2)	0.0140 (19)
C13	0.101 (3)	0.068 (2)	0.083 (3)	0.004 (2)	0.014 (2)	0.018 (2)
C14	0.099 (3)	0.070 (2)	0.088 (3)	−0.006 (2)	0.009 (2)	0.008 (2)
C15	0.091 (2)	0.0497 (18)	0.079 (2)	−0.0087 (18)	0.012 (2)	−0.0058 (18)
C16	0.070 (2)	0.0446 (17)	0.070 (2)	0.0015 (15)	0.0234 (18)	0.0022 (15)
C17	0.073 (2)	0.0402 (16)	0.072 (2)	0.0004 (16)	0.0197 (18)	0.0004 (16)
C18	0.082 (2)	0.055 (2)	0.069 (2)	0.0013 (19)	0.015 (2)	−0.0019 (18)
C19	0.097 (3)	0.075 (2)	0.079 (2)	−0.008 (2)	0.008 (2)	0.0001 (19)
C20	0.103 (3)	0.096 (3)	0.092 (3)	0.000 (2)	0.010 (2)	0.010 (2)

O1—C1	1.358 (3)	O4—C11	1.369 (3)
O1—H1	0.82	O4—H4A	0.82
O2—C8	1.220 (3)	O5—C18	1.205 (3)
O3—C8	1.338 (3)	O6—C18	1.348 (3)
O3—C9	1.447 (3)	O6—C19	1.454 (3)
N1—C7	1.289 (3)	N3—C17	1.274 (3)
N1—N2	1.365 (3)	N3—N4	1.369 (3)
N2—C8	1.363 (3)	N4—C18	1.355 (3)
N2—H2A	0.86	N4—H6	0.86
C1—C2	1.368 (4)	C11—C12	1.381 (4)
C1—C6	1.414 (4)	C11—C16	1.418 (4)
C2—C3	1.382 (4)	C12—C13	1.379 (4)
C2—H2	0.95	C12—H12	0.95
C3—C4	1.391 (4)	C13—C14	1.400 (4)
C3—H3	0.95	C13—H13	0.95
C4—C5	1.371 (4)	C14—C15	1.384 (4)
C4—H4	0.95	C14—H14	0.95
C5—C6	1.395 (4)	C15—C16	1.395 (4)
C5—H5	0.95	C15—H15	0.95
C6—C7	1.436 (4)	C16—C17	1.458 (4)
C7—H7A	0.95	C17—H17	0.95
C9—C10	1.491 (4)	C19—C20	1.495 (4)
C9—H9A	0.99	C19—H19A	0.99
C9—H9B	0.99	C19—H19B	0.99
C10—H10A	0.98	C20—H20A	0.98
C10—H10B	0.98	C20—H20B	0.98
C10—H10C	0.98	C20—H20C	0.98
C1—O1—H1	109.4	C11—O4—H4A	109.4
C8—O3—C9	116.4 (2)	C18—O6—C19	114.9 (2)
C7—N1—N2	119.9 (2)	C17—N3—N4	120.9 (2)
C8—N2—N1	117.8 (2)	C18—N4—N3	116.1 (2)
C8—N2—H2A	121.2	C18—N4—H6	122.0
N1—N2—H2A	121.0	N3—N4—H6	121.9
O1—C1—C2	118.8 (3)	O4—C11—C12	118.4 (3)
O1—C1—C6	121.0 (3)	O4—C11—C16	121.4 (3)
C2—C1—C6	120.2 (3)	C12—C11—C16	120.3 (3)
C1—C2—C3	121.2 (3)	C13—C12—C11	120.5 (3)
C1—C2—H2	119.4	C13—C12—H12	119.7
C3—C2—H2	119.4	C11—C12—H12	119.7
C2—C3—C4	120.0 (3)	C12—C13—C14	120.7 (3)
C2—C3—H3	120.0	C12—C13—H13	119.6
C4—C3—H3	120.0	C14—C13—H13	119.6
C5—C4—C3	118.7 (3)	C15—C14—C13	118.4 (3)
C5—C4—H4	120.7	C15—C14—H14	120.8
C3—C4—H4	120.7	C13—C14—H14	120.8
C4—C5—C6	122.8 (3)	C14—C15—C16	122.4 (3)
C4—C5—H5	118.6	C14—C15—H15	118.8
C6—C5—H5	118.6	C16—C15—H15	118.8
C5—C6—C1	117.1 (3)	C15—C16—C11	117.6 (3)
C5—C6—C7	120.7 (3)	C15—C16—C17	120.4 (3)
C1—C6—C7	122.1 (3)	C11—C16—C17	121.9 (3)
N1—C7—C6	120.0 (3)	N3—C17—C16	119.8 (3)
N1—C7—H7A	120.0	N3—C17—H17	120.1
C6—C7—H7A	120.0	C16—C17—H17	120.1
O2—C8—O3	125.7 (3)	O5—C18—O6	125.3 (3)
O2—C8—N2	124.3 (3)	O5—C18—N4	124.8 (3)
O3—C8—N2	110.0 (3)	O6—C18—N4	110.0 (3)
O3—C9—C10	107.9 (3)	O6—C19—C20	107.7 (3)
O3—C9—H9A	110.1	O6—C19—H19A	110.2
C10—C9—H9A	110.1	C20—C19—H19A	110.2
O3—C9—H9B	110.1	O6—C19—H19B	110.2
C10—C9—H9B	110.1	C20—C19—H19B	110.2
H9A—C9—H9B	108.4	H19A—C19—H19B	108.5
C9—C10—H10A	109.5	C19—C20—H20A	109.5
C9—C10—H10B	109.5	C19—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C9—C10—H10C	109.5	C19—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.573 (3)	147
N2—H2A···O4i	0.86	2.13	2.979 (4)	170
O4—H4A···N3	0.82	1.86	2.586 (3)	146
N4—H6···O2ii	0.86	2.08	2.931 (4)	170
C5—H5···O5i	0.95	2.27	3.184 (4)	161
C15—H15···O1ii	0.95	2.46	3.371 (5)	161

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	2.573 (3)	147
N2—H2A⋯O4i	0.86	2.13	2.979 (4)	170
O4—H4A⋯N3	0.82	1.86	2.586 (3)	146
N4—H6⋯O2ii	0.86	2.08	2.931 (4)	170
C5—H5⋯O5i	0.95	2.27	3.184 (4)	161
C15—H15⋯O1ii	0.95	2.46	3.371 (5)	161

Symmetry codes: (i) ; (ii) .