(E)-2-(4-Hy-droxy-3-meth-oxy-benzyl-idene)hydrazinecarboxamide.

The asymmetric unit of the title compound, C(9)H(11)N(3)O(3), consists of two crystallographically independent mol-ecules. Both mol-ecules are almost planar, with r.m.s. deviations of 0.107 and 0.099 Å. In the crystal, the two independent mol-ecules form a dimer with an R(2) (2)(8) ring motif via N-H⋯O hydrogen bonds. The dimers are further linked into a three-dimensional network by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For applications of semicarbazone derivatives, see: Warren et al. (1977 ▶); Chandra & Gupta (2005 ▶); Jain et al. (2002 ▶); Pilgram (1978 ▶); Yogeeswari et al. (2004 ▶). For the synthesis, see: Vogel et al. (1978 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11N3O3

M = 209.21

Orthorhombic,

a = 13.8568 (3) Å

b = 5.0379 (1) Å

c = 26.8582 (5) Å

V = 1874.95 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.56 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.939, T max = 0.992

27088 measured reflections

3785 independent reflections

3477 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.05

3785 reflections

305 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024068/is2735sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024068/is2735Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024068/is2735Isup3.cml

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

C9H11N3O3	F(000) = 880
Mr = 209.21	Dx = 1.482 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 8792 reflections
a = 13.8568 (3) Å	θ = 3.0–33.7°
b = 5.0379 (1) Å	µ = 0.11 mm−1
c = 26.8582 (5) Å	T = 100 K
V = 1874.95 (7) Å3	Plate, colourless
Z = 8	0.56 × 0.21 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	3785 independent reflections
Radiation source: fine-focus sealed tube	3477 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 33.8°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.939, Tmax = 0.992	k = −7→7
27088 measured reflections	l = −42→34

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2848P] where P = (Fo2 + 2Fc2)/3
3785 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A	0.36344 (8)	1.9545 (3)	0.42045 (5)	0.0210 (2)
O2A	0.17592 (9)	1.9564 (2)	0.43391 (5)	0.0184 (2)
H2OA	0.220 (2)	2.071 (6)	0.4406 (12)	0.039 (8)*
O3A	0.56955 (8)	0.7961 (2)	0.21626 (5)	0.0197 (2)
N1A	0.42454 (10)	1.2040 (3)	0.29115 (5)	0.0167 (2)
N2A	0.45328 (10)	0.9953 (3)	0.26135 (6)	0.0176 (3)
H2NA	0.411 (2)	0.885 (6)	0.2484 (11)	0.034 (7)*
N3A	0.60407 (11)	1.1886 (3)	0.25456 (6)	0.0203 (3)
H3NA	0.581 (2)	1.323 (6)	0.2682 (12)	0.041 (8)*
H3NB	0.6599 (18)	1.207 (5)	0.2389 (10)	0.025 (6)*
C1A	0.35450 (11)	1.5891 (3)	0.36049 (6)	0.0156 (3)
H1A	0.4220	1.5897	0.3544	0.019*
C2A	0.31448 (10)	1.7697 (3)	0.39336 (6)	0.0144 (3)
C3A	0.21404 (11)	1.7756 (3)	0.40168 (6)	0.0148 (3)
C4A	0.15552 (11)	1.5929 (3)	0.37808 (6)	0.0173 (3)
H4A	0.0879	1.5941	0.3839	0.021*
C5A	0.19573 (11)	1.4062 (3)	0.34560 (6)	0.0170 (3)
H5A	0.1553	1.2793	0.3298	0.020*
C6A	0.29452 (11)	1.4047 (3)	0.33624 (6)	0.0152 (3)
C7A	0.33449 (12)	1.2052 (3)	0.30250 (6)	0.0165 (3)
H7A	0.2931	1.0740	0.2887	0.020*
C8A	0.54501 (11)	0.9882 (3)	0.24256 (6)	0.0156 (3)
C9A	0.46611 (11)	1.9590 (4)	0.41561 (7)	0.0213 (3)
H9AA	0.4930	2.0937	0.4380	0.032*
H9AB	0.4834	2.0020	0.3812	0.032*
H9AC	0.4923	1.7845	0.4244	0.032*
O1B	0.53465 (8)	−0.4555 (2)	0.01033 (5)	0.0185 (2)
O2B	0.72055 (9)	−0.3736 (3)	−0.00747 (5)	0.0207 (2)
H1OB	0.6814 (19)	−0.481 (5)	−0.0197 (11)	0.031 (7)*
O3B	0.29971 (9)	0.6842 (2)	0.21721 (5)	0.0191 (2)
N1B	0.44745 (10)	0.2792 (3)	0.14260 (5)	0.0161 (2)
N2B	0.41711 (10)	0.4832 (3)	0.17293 (5)	0.0177 (3)
H2NB	0.4597 (19)	0.600 (5)	0.1853 (10)	0.029 (6)*
N3B	0.26476 (11)	0.2964 (3)	0.17689 (6)	0.0203 (3)
H3ND	0.2088 (18)	0.283 (5)	0.1902 (10)	0.026 (6)*
H3NC	0.288 (2)	0.162 (6)	0.1622 (11)	0.038 (8)*
C1B	0.53046 (11)	−0.0990 (3)	0.07266 (6)	0.0154 (3)
H1B	0.4640	−0.1245	0.0799	0.019*
C2B	0.57608 (10)	−0.2581 (3)	0.03781 (6)	0.0144 (3)
C3B	0.67512 (11)	−0.2216 (3)	0.02783 (6)	0.0156 (3)
C4B	0.72711 (11)	−0.0285 (3)	0.05253 (6)	0.0174 (3)
H4B	0.7940	−0.0062	0.0459	0.021*
C5B	0.68118 (11)	0.1338 (3)	0.08729 (6)	0.0169 (3)
H5B	0.7168	0.2673	0.1042	0.020*
C6B	0.58328 (11)	0.1011 (3)	0.09736 (6)	0.0148 (3)
C7B	0.53818 (11)	0.2863 (3)	0.13190 (6)	0.0157 (3)
H7B	0.5773	0.4180	0.1472	0.019*
C8B	0.32466 (11)	0.4926 (3)	0.19051 (6)	0.0152 (3)
C9B	0.43242 (11)	−0.4943 (3)	0.01562 (7)	0.0192 (3)
H9BA	0.4123	−0.6471	−0.0044	0.029*
H9BB	0.3983	−0.3351	0.0042	0.029*
H9BC	0.4170	−0.5272	0.0507	0.029*

	U11	U22	U33	U12	U13	U23
O1A	0.0126 (5)	0.0269 (6)	0.0234 (6)	−0.0001 (4)	−0.0005 (4)	−0.0095 (5)
O2A	0.0139 (5)	0.0211 (5)	0.0201 (6)	0.0010 (4)	0.0028 (4)	−0.0038 (4)
O3A	0.0163 (5)	0.0177 (5)	0.0250 (6)	−0.0002 (4)	0.0041 (4)	−0.0053 (5)
N1A	0.0182 (6)	0.0160 (5)	0.0160 (6)	0.0016 (4)	0.0019 (5)	−0.0029 (4)
N2A	0.0147 (6)	0.0173 (6)	0.0209 (6)	−0.0013 (4)	0.0041 (5)	−0.0056 (5)
N3A	0.0161 (6)	0.0185 (6)	0.0261 (7)	−0.0022 (5)	0.0036 (5)	−0.0058 (5)
C1A	0.0130 (6)	0.0177 (6)	0.0161 (6)	0.0014 (5)	0.0011 (5)	−0.0006 (5)
C2A	0.0117 (6)	0.0178 (6)	0.0137 (6)	−0.0003 (5)	−0.0007 (5)	0.0001 (5)
C3A	0.0133 (6)	0.0167 (6)	0.0144 (6)	0.0022 (5)	0.0013 (5)	0.0010 (5)
C4A	0.0122 (6)	0.0198 (6)	0.0199 (7)	0.0001 (5)	0.0015 (5)	0.0000 (5)
C5A	0.0141 (6)	0.0180 (6)	0.0188 (7)	−0.0004 (5)	−0.0001 (5)	−0.0012 (5)
C6A	0.0148 (6)	0.0161 (6)	0.0146 (6)	0.0008 (5)	0.0005 (5)	0.0000 (5)
C7A	0.0167 (6)	0.0172 (6)	0.0154 (6)	0.0011 (5)	0.0001 (5)	−0.0012 (5)
C8A	0.0150 (6)	0.0161 (6)	0.0155 (6)	0.0014 (5)	0.0000 (5)	0.0009 (5)
C9A	0.0135 (6)	0.0280 (7)	0.0223 (7)	−0.0024 (5)	0.0004 (6)	−0.0044 (6)
O1B	0.0143 (5)	0.0201 (5)	0.0212 (6)	−0.0006 (4)	0.0002 (4)	−0.0053 (4)
O2B	0.0160 (5)	0.0247 (5)	0.0213 (6)	0.0017 (4)	0.0021 (4)	−0.0074 (5)
O3B	0.0166 (5)	0.0170 (5)	0.0236 (6)	0.0011 (4)	0.0038 (4)	−0.0046 (4)
N1B	0.0168 (6)	0.0162 (5)	0.0154 (6)	0.0010 (4)	0.0024 (5)	−0.0027 (4)
N2B	0.0144 (6)	0.0181 (5)	0.0206 (6)	−0.0011 (4)	0.0038 (5)	−0.0059 (5)
N3B	0.0166 (6)	0.0186 (6)	0.0258 (7)	−0.0018 (5)	0.0032 (5)	−0.0055 (5)
C1B	0.0135 (6)	0.0177 (6)	0.0151 (6)	0.0006 (5)	0.0007 (5)	−0.0005 (5)
C2B	0.0126 (6)	0.0156 (6)	0.0151 (6)	0.0007 (5)	0.0001 (5)	−0.0004 (5)
C3B	0.0149 (6)	0.0174 (6)	0.0145 (6)	0.0028 (5)	0.0017 (5)	−0.0013 (5)
C4B	0.0135 (6)	0.0206 (6)	0.0181 (7)	0.0013 (5)	0.0012 (5)	−0.0010 (5)
C5B	0.0151 (6)	0.0190 (6)	0.0167 (7)	−0.0002 (5)	0.0002 (5)	−0.0005 (5)
C6B	0.0154 (6)	0.0160 (6)	0.0131 (6)	0.0016 (5)	0.0009 (5)	−0.0002 (5)
C7B	0.0164 (6)	0.0166 (6)	0.0140 (6)	0.0000 (5)	0.0005 (5)	−0.0008 (5)
C8B	0.0151 (6)	0.0153 (6)	0.0152 (6)	0.0011 (5)	0.0014 (5)	0.0000 (5)
C9B	0.0139 (6)	0.0232 (7)	0.0206 (7)	−0.0019 (5)	−0.0013 (5)	−0.0009 (5)

O1A—C2A	1.3626 (19)	O1B—C2B	1.3651 (18)
O1A—C9A	1.429 (2)	O1B—C9B	1.4370 (19)
O2A—C3A	1.3630 (19)	O2B—C3B	1.3717 (19)
O2A—H2OA	0.86 (3)	O2B—H1OB	0.83 (3)
O3A—C8A	1.2458 (19)	O3B—C8B	1.2511 (18)
N1A—C7A	1.285 (2)	N1B—C7B	1.290 (2)
N1A—N2A	1.3801 (19)	N1B—N2B	1.3772 (18)
N2A—C8A	1.368 (2)	N2B—C8B	1.3661 (19)
N2A—H2NA	0.88 (3)	N2B—H2NB	0.90 (3)
N3A—C8A	1.339 (2)	N3B—C8B	1.341 (2)
N3A—H3NA	0.83 (3)	N3B—H3ND	0.86 (3)
N3A—H3NB	0.89 (3)	N3B—H3NC	0.85 (3)
C1A—C2A	1.384 (2)	C1B—C2B	1.385 (2)
C1A—C6A	1.406 (2)	C1B—C6B	1.411 (2)
C1A—H1A	0.9500	C1B—H1B	0.9500
C2A—C3A	1.410 (2)	C2B—C3B	1.410 (2)
C3A—C4A	1.381 (2)	C3B—C4B	1.380 (2)
C4A—C5A	1.399 (2)	C4B—C5B	1.395 (2)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.392 (2)	C5B—C6B	1.393 (2)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.462 (2)	C6B—C7B	1.457 (2)
C7A—H7A	0.9500	C7B—H7B	0.9500
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C2A—O1A—C9A	117.26 (12)	C2B—O1B—C9B	117.40 (12)
C3A—O2A—H2OA	108 (2)	C3B—O2B—H1OB	109.6 (19)
C7A—N1A—N2A	114.92 (13)	C7B—N1B—N2B	114.11 (13)
C8A—N2A—N1A	120.12 (13)	C8B—N2B—N1B	121.10 (13)
C8A—N2A—H2NA	117.1 (19)	C8B—N2B—H2NB	117.9 (17)
N1A—N2A—H2NA	121.3 (18)	N1B—N2B—H2NB	120.4 (17)
C8A—N3A—H3NA	119 (2)	C8B—N3B—H3ND	120.2 (17)
C8A—N3A—H3NB	119.9 (17)	C8B—N3B—H3NC	118.5 (19)
H3NA—N3A—H3NB	117 (3)	H3ND—N3B—H3NC	119 (2)
C2A—C1A—C6A	119.54 (14)	C2B—C1B—C6B	119.62 (13)
C2A—C1A—H1A	120.2	C2B—C1B—H1B	120.2
C6A—C1A—H1A	120.2	C6B—C1B—H1B	120.2
O1A—C2A—C1A	126.19 (13)	O1B—C2B—C1B	126.52 (13)
O1A—C2A—C3A	113.11 (13)	O1B—C2B—C3B	113.67 (13)
C1A—C2A—C3A	120.70 (14)	C1B—C2B—C3B	119.82 (13)
O2A—C3A—C4A	120.61 (14)	O2B—C3B—C4B	119.08 (13)
O2A—C3A—C2A	119.82 (14)	O2B—C3B—C2B	120.34 (13)
C4A—C3A—C2A	119.54 (14)	C4B—C3B—C2B	120.56 (14)
C3A—C4A—C5A	120.05 (14)	C3B—C4B—C5B	119.78 (14)
C3A—C4A—H4A	120.0	C3B—C4B—H4B	120.1
C5A—C4A—H4A	120.0	C5B—C4B—H4B	120.1
C6A—C5A—C4A	120.52 (14)	C6B—C5B—C4B	120.33 (14)
C6A—C5A—H5A	119.7	C6B—C5B—H5B	119.8
C4A—C5A—H5A	119.7	C4B—C5B—H5B	119.8
C5A—C6A—C1A	119.62 (14)	C5B—C6B—C1B	119.88 (14)
C5A—C6A—C7A	119.20 (14)	C5B—C6B—C7B	117.75 (14)
C1A—C6A—C7A	121.15 (14)	C1B—C6B—C7B	122.30 (14)
N1A—C7A—C6A	121.20 (14)	N1B—C7B—C6B	122.82 (14)
N1A—C7A—H7A	119.4	N1B—C7B—H7B	118.6
C6A—C7A—H7A	119.4	C6B—C7B—H7B	118.6
O3A—C8A—N3A	123.75 (15)	O3B—C8B—N3B	123.62 (15)
O3A—C8A—N2A	118.88 (14)	O3B—C8B—N2B	118.94 (14)
N3A—C8A—N2A	117.36 (14)	N3B—C8B—N2B	117.42 (14)
O1A—C9A—H9AA	109.5	O1B—C9B—H9BA	109.5
O1A—C9A—H9AB	109.5	O1B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
O1A—C9A—H9AC	109.5	O1B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C7A—N1A—N2A—C8A	173.09 (15)	C7B—N1B—N2B—C8B	−175.20 (15)
C9A—O1A—C2A—C1A	−1.7 (2)	C9B—O1B—C2B—C1B	3.9 (2)
C9A—O1A—C2A—C3A	178.26 (14)	C9B—O1B—C2B—C3B	−175.85 (14)
C6A—C1A—C2A—O1A	178.16 (15)	C6B—C1B—C2B—O1B	−178.73 (14)
C6A—C1A—C2A—C3A	−1.8 (2)	C6B—C1B—C2B—C3B	1.0 (2)
O1A—C2A—C3A—O2A	0.6 (2)	O1B—C2B—C3B—O2B	1.3 (2)
C1A—C2A—C3A—O2A	−179.49 (14)	C1B—C2B—C3B—O2B	−178.42 (14)
O1A—C2A—C3A—C4A	−177.67 (14)	O1B—C2B—C3B—C4B	179.73 (14)
C1A—C2A—C3A—C4A	2.3 (2)	C1B—C2B—C3B—C4B	0.0 (2)
O2A—C3A—C4A—C5A	−179.16 (15)	O2B—C3B—C4B—C5B	177.80 (14)
C2A—C3A—C4A—C5A	−0.9 (2)	C2B—C3B—C4B—C5B	−0.6 (2)
C3A—C4A—C5A—C6A	−0.9 (2)	C3B—C4B—C5B—C6B	0.3 (2)
C4A—C5A—C6A—C1A	1.3 (2)	C4B—C5B—C6B—C1B	0.7 (2)
C4A—C5A—C6A—C7A	179.36 (15)	C4B—C5B—C6B—C7B	−176.57 (14)
C2A—C1A—C6A—C5A	0.0 (2)	C2B—C1B—C6B—C5B	−1.3 (2)
C2A—C1A—C6A—C7A	−177.99 (15)	C2B—C1B—C6B—C7B	175.81 (14)
N2A—N1A—C7A—C6A	176.29 (14)	N2B—N1B—C7B—C6B	−175.18 (14)
C5A—C6A—C7A—N1A	176.93 (15)	C5B—C6B—C7B—N1B	177.73 (15)
C1A—C6A—C7A—N1A	−5.1 (2)	C1B—C6B—C7B—N1B	0.6 (2)
N1A—N2A—C8A—O3A	179.13 (15)	N1B—N2B—C8B—O3B	−178.70 (15)
N1A—N2A—C8A—N3A	0.4 (2)	N1B—N2B—C8B—N3B	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2OA···O2Bi	0.86 (3)	2.22 (3)	2.9924 (18)	149 (3)
N2A—H2NA···O3B	0.88 (3)	2.03 (3)	2.8966 (19)	171 (3)
N3A—H3NB···O3Bii	0.89 (3)	2.10 (3)	2.961 (2)	165 (2)
N2B—H2NB···O3A	0.90 (3)	2.00 (3)	2.8812 (18)	169 (2)
N3B—H3ND···O3Aiii	0.86 (3)	2.09 (3)	2.9415 (19)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2OA⋯O2Bi	0.86 (3)	2.22 (3)	2.9924 (18)	149 (3)
N2A—H2NA⋯O3B	0.88 (3)	2.03 (3)	2.8966 (19)	171 (3)
N3A—H3NB⋯O3Bii	0.89 (3)	2.10 (3)	2.961 (2)	165 (2)
N2B—H2NB⋯O3A	0.90 (3)	2.00 (3)	2.8812 (18)	169 (2)
N3B—H3ND⋯O3Aiii	0.86 (3)	2.09 (3)	2.9415 (19)	172 (3)

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