(E)-Methyl N'-(2-hydroxy-benzyl-idene)-hydrazinecarboxyl-ate at 123 K.

In the title mol-ecule, C(9)H(10)N(2)O(3), the hydrazinecarboxylic acid mean plane and the benzene ring form a dihedral angle of 11.1 (1)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains extending along the b axis. An intra-molecular O-H⋯N hydrogen bond is also present.

Related literature

For applications of benzaldehyde­hydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For related structures, see: Cheng (2008 ▶).

Experimental

Crystal data

C9H10N2O3

M = 194.19

Orthorhombic,

a = 9.3998 (17) Å

b = 9.0945 (16) Å

c = 22.319 (4) Å

V = 1908.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 123 (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 = 0.965, T max = 0.968

18306 measured reflections

1679 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.120

S = 1.05

1679 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.19 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/S1600536808022332/cv2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022332/cv2431Isup2.hkl

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

C9H10N2O3	F000 = 816
Mr = 194.19	Dx = 1.352 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1679 reflections
a = 9.3998 (17) Å	θ = 2.0–25.0º
b = 9.0945 (16) Å	µ = 0.10 mm−1
c = 22.319 (4) Å	T = 123 (2) K
V = 1908.0 (6) Å3	Block, colourless
Z = 8	0.27 × 0.24 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	1679 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 123(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −10→11
Tmin = 0.965, Tmax = 0.968	k = −10→10
18306 measured reflections	l = −26→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.4536P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max = 0.028
S = 1.05	Δρmax = 0.19 e Å−3
1679 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: 0.018 (2)
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
O3	0.37197 (12)	0.41375 (11)	−0.07538 (5)	0.0513 (3)
O2	0.36215 (12)	0.62287 (11)	−0.02044 (5)	0.0576 (4)
O1	0.16149 (12)	0.69567 (13)	0.13213 (5)	0.0625 (4)
H1	0.1906	0.6525	0.1012	0.094*
N2	0.22056 (13)	0.42471 (13)	−0.00032 (5)	0.0480 (4)
H2	0.1929	0.3365	−0.0116	0.058*
N1	0.16212 (12)	0.49157 (13)	0.04907 (5)	0.0452 (3)
C6	−0.00199 (15)	0.48908 (16)	0.13011 (6)	0.0429 (4)
C8	0.32185 (15)	0.49856 (15)	−0.03107 (6)	0.0431 (4)
C5	0.05028 (15)	0.61971 (16)	0.15591 (6)	0.0459 (4)
C7	0.06038 (16)	0.42561 (15)	0.07632 (6)	0.0461 (4)
H7	0.0255	0.3347	0.0613	0.055*
C1	−0.01226 (17)	0.67565 (18)	0.20764 (7)	0.0558 (4)
H1A	0.0236	0.7634	0.2251	0.067*
C4	−0.11726 (17)	0.41942 (18)	0.15784 (7)	0.0527 (4)
H4	−0.1537	0.3311	0.1411	0.063*
C2	−0.12633 (18)	0.6040 (2)	0.23379 (7)	0.0568 (5)
H2A	−0.1685	0.6431	0.2690	0.068*
C3	−0.17925 (17)	0.4760 (2)	0.20895 (7)	0.0573 (4)
H3	−0.2577	0.4272	0.2269	0.069*
C9	0.47848 (19)	0.4811 (2)	−0.11312 (7)	0.0617 (5)
H9A	0.5081	0.4111	−0.1441	0.093*
H9B	0.5610	0.5087	−0.0887	0.093*
H9C	0.4386	0.5690	−0.1321	0.093*

	U11	U22	U33	U12	U13	U23
O3	0.0596 (7)	0.0459 (6)	0.0484 (6)	0.0025 (5)	0.0093 (5)	−0.0070 (4)
O2	0.0665 (7)	0.0388 (6)	0.0674 (7)	−0.0022 (5)	0.0054 (5)	−0.0070 (5)
O1	0.0605 (7)	0.0593 (7)	0.0678 (7)	−0.0134 (5)	0.0108 (5)	−0.0181 (6)
N2	0.0567 (8)	0.0389 (7)	0.0484 (7)	−0.0020 (5)	0.0070 (6)	−0.0121 (5)
N1	0.0476 (7)	0.0430 (7)	0.0451 (7)	0.0051 (5)	0.0001 (5)	−0.0081 (5)
C6	0.0434 (8)	0.0435 (8)	0.0419 (8)	0.0047 (6)	−0.0069 (6)	0.0001 (6)
C8	0.0478 (8)	0.0366 (7)	0.0448 (8)	0.0075 (6)	−0.0035 (6)	−0.0040 (6)
C5	0.0457 (8)	0.0472 (8)	0.0449 (8)	0.0032 (6)	−0.0052 (6)	−0.0023 (6)
C7	0.0491 (8)	0.0406 (8)	0.0487 (8)	−0.0001 (6)	−0.0032 (6)	−0.0054 (6)
C1	0.0603 (10)	0.0578 (10)	0.0491 (8)	0.0048 (8)	−0.0057 (7)	−0.0124 (7)
C4	0.0526 (9)	0.0508 (9)	0.0548 (9)	−0.0005 (7)	−0.0012 (7)	−0.0002 (7)
C2	0.0586 (9)	0.0722 (11)	0.0395 (8)	0.0159 (8)	−0.0004 (7)	−0.0001 (7)
C3	0.0530 (9)	0.0651 (10)	0.0536 (9)	0.0043 (8)	0.0057 (7)	0.0105 (8)
C9	0.0589 (10)	0.0734 (11)	0.0528 (9)	0.0014 (8)	0.0107 (7)	0.0036 (8)

O3—C8	1.3397 (17)	C5—C1	1.392 (2)
O3—C9	1.4445 (19)	C7—H7	0.9500
O2—C8	1.2158 (18)	C1—C2	1.384 (2)
O1—C5	1.3607 (18)	C1—H1A	0.9500
O1—H1	0.8400	C4—C3	1.380 (2)
N2—C8	1.3522 (19)	C4—H4	0.9500
N2—N1	1.3736 (16)	C2—C3	1.383 (3)
N2—H2	0.8800	C2—H2A	0.9500
N1—C7	1.2823 (19)	C3—H3	0.9500
C6—C4	1.399 (2)	C9—H9A	0.9800
C6—C5	1.409 (2)	C9—H9B	0.9800
C6—C7	1.455 (2)	C9—H9C	0.9800
C8—O3—C9	115.49 (12)	C2—C1—C5	120.34 (15)
C5—O1—H1	109.5	C2—C1—H1A	119.8
C8—N2—N1	117.97 (12)	C5—C1—H1A	119.8
C8—N2—H2	121.0	C3—C4—C6	121.58 (15)
N1—N2—H2	121.0	C3—C4—H4	119.2
C7—N1—N2	118.15 (12)	C6—C4—H4	119.2
C4—C6—C5	118.10 (14)	C3—C2—C1	120.42 (15)
C4—C6—C7	119.81 (13)	C3—C2—H2A	119.8
C5—C6—C7	122.09 (14)	C1—C2—H2A	119.8
O2—C8—O3	124.74 (14)	C4—C3—C2	119.56 (16)
O2—C8—N2	125.61 (14)	C4—C3—H3	120.2
O3—C8—N2	109.65 (12)	C2—C3—H3	120.2
O1—C5—C1	117.55 (13)	O3—C9—H9A	109.5
O1—C5—C6	122.45 (13)	O3—C9—H9B	109.5
C1—C5—C6	120.00 (14)	H9A—C9—H9B	109.5
N1—C7—C6	120.40 (13)	O3—C9—H9C	109.5
N1—C7—H7	119.8	H9A—C9—H9C	109.5
C6—C7—H7	119.8	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.89	2.6234 (16)	145
N2—H2···O2i	0.88	2.02	2.8881 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.89	2.6234 (16)	145
N2—H2⋯O2i	0.88	2.02	2.8881 (16)	169

Symmetry code: (i) .