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

In the title compound, C(9)H(11)N(3)O(3), two mol-ecules are present in the asymmetric unit in which the 4-hy-droxy-3-meth-oxy-benzaldehyde and hydrazinecarboxamide units are almost planar [with r.m.s. deviations 0.0212 and 0.0066 Å, respectively, in one mol-ecule and 0.0346 and 0.0095 Å, respectively, in the other] and are oriented at dihedral angles of 9.7 (3) and 16.6 (3)°. In both mol-ecules, two S(5) ring motifs are present due to N-H⋯N and O-H⋯O hydrogen bonds. In the crystal, the mol-ecules are dimerized with each other due to pairs of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. O-H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For a related structure, see: Tahir et al. (2012 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11N3O3

M = 209.21

Orthorhombic,

a = 13.9945 (14) Å

b = 5.0440 (4) Å

c = 27.286 (2) Å

V = 1926.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.966

8297 measured reflections

1931 independent reflections

1046 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.113

S = 0.98

1931 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025299/bq2364sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025299/bq2364Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025299/bq2364Isup3.cml

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

C9H11N3O3	F(000) = 880
Mr = 209.21	Dx = 1.443 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2704 reflections
a = 13.9945 (14) Å	θ = 1.8–26.0°
b = 5.0440 (4) Å	µ = 0.11 mm−1
c = 27.286 (2) Å	T = 296 K
V = 1926.0 (3) Å3	Needle, colorless
Z = 8	0.30 × 0.16 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	1931 independent reflections
Radiation source: fine-focus sealed tube	1046 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −3→6
Tmin = 0.957, Tmax = 0.966	l = −33→33
8297 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3
1931 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.1256 (3)	−0.4282 (10)	0.51673 (17)	0.051 (2)
O2	0.3120 (3)	−0.4570 (10)	0.52664 (17)	0.0437 (19)
O3	−0.0668 (3)	0.7125 (10)	0.3095 (2)	0.0423 (16)
N1	0.0730 (4)	0.3033 (11)	0.38554 (19)	0.035 (2)
N2	0.0463 (3)	0.5085 (12)	0.3552 (2)	0.041 (2)
N3	−0.1032 (4)	0.3268 (12)	0.3479 (2)	0.048 (2)
C1	0.1988 (4)	0.0965 (14)	0.4299 (2)	0.031 (3)
C2	0.1392 (5)	−0.0745 (13)	0.4553 (3)	0.035 (3)
C3	0.1765 (4)	−0.2580 (13)	0.4879 (2)	0.031 (3)
C4	0.2739 (5)	−0.2735 (12)	0.4950 (2)	0.031 (2)
C5	0.3343 (4)	−0.1063 (13)	0.4703 (2)	0.039 (3)
C6	0.2965 (4)	0.0792 (13)	0.4384 (2)	0.037 (3)
C7	0.0252 (4)	−0.4398 (15)	0.5100 (3)	0.049 (3)
C8	0.1602 (5)	0.2916 (13)	0.3966 (2)	0.032 (2)
C9	−0.0445 (4)	0.5255 (14)	0.3362 (2)	0.031 (2)
O4	−0.0199 (3)	0.9504 (9)	0.10503 (17)	0.0413 (16)
O5	−0.2032 (3)	0.8811 (10)	0.08760 (18)	0.049 (2)
O6	0.2021 (3)	−0.1888 (9)	0.31097 (17)	0.0430 (17)
N4	0.0595 (3)	0.2198 (10)	0.23612 (18)	0.0307 (17)
N5	0.0884 (4)	0.0189 (11)	0.2668 (2)	0.040 (2)
N6	0.2384 (4)	0.1926 (10)	0.2705 (2)	0.044 (2)
C10	−0.0733 (4)	0.4019 (13)	0.1914 (2)	0.031 (2)
C11	−0.0188 (4)	0.5961 (13)	0.1670 (2)	0.029 (2)
C12	−0.0626 (5)	0.7582 (13)	0.1326 (2)	0.030 (2)
C13	−0.1603 (4)	0.7257 (13)	0.1226 (2)	0.032 (3)
C14	−0.2137 (5)	0.5398 (14)	0.1471 (3)	0.038 (3)
C15	−0.1697 (4)	0.3796 (13)	0.1809 (2)	0.035 (2)
C16	0.0808 (4)	0.9841 (14)	0.1099 (3)	0.045 (3)
C17	−0.0297 (4)	0.2151 (12)	0.2254 (2)	0.030 (2)
C18	0.1785 (5)	0.0009 (15)	0.2845 (2)	0.033 (2)
H2	0.07352	−0.06591	0.45048	0.0424*
H2A	0.26884	−0.54591	0.53860	0.0649*
H2B	0.08747	0.62892	0.34795	0.0490*
H3A	−0.16059	0.32439	0.33656	0.0569*
H3B	−0.08372	0.20124	0.36668	0.0569*
H5	0.40001	−0.11747	0.47486	0.0464*
H6	0.33740	0.19515	0.42224	0.0444*
H7A	0.01136	−0.49086	0.47685	0.0593*
H7B	−0.00207	−0.26864	0.51642	0.0593*
H7C	−0.00159	−0.56760	0.53213	0.0593*
H8	0.20166	0.41433	0.38265	0.0377*
H5A	−0.16623	0.99847	0.07909	0.0729*
H5B	0.04750	−0.10020	0.27510	0.0479*
H6A	0.29709	0.18908	0.27988	0.0534*
H6B	0.21835	0.31947	0.25217	0.0534*
H11	0.04595	0.61546	0.17385	0.0351*
H14	−0.27877	0.52269	0.14088	0.0458*
H15	−0.20577	0.25249	0.19730	0.0421*
H16A	0.11246	0.81983	0.10266	0.0675*
H16B	0.09561	1.03701	0.14284	0.0675*
H16C	0.10226	1.11826	0.08749	0.0675*
H17	−0.06819	0.08711	0.23996	0.0368*

	U11	U22	U33	U12	U13	U23
O1	0.028 (3)	0.070 (4)	0.055 (4)	−0.003 (3)	−0.004 (3)	0.032 (3)
O2	0.030 (3)	0.052 (4)	0.049 (3)	0.005 (2)	−0.003 (2)	0.013 (3)
O3	0.028 (2)	0.039 (3)	0.060 (3)	0.000 (2)	−0.011 (2)	0.016 (3)
N1	0.031 (3)	0.031 (4)	0.042 (4)	0.001 (3)	−0.010 (3)	0.012 (3)
N2	0.024 (3)	0.036 (4)	0.062 (4)	−0.005 (3)	−0.013 (3)	0.013 (3)
N3	0.026 (3)	0.055 (5)	0.062 (4)	−0.003 (3)	−0.010 (3)	0.020 (4)
C1	0.025 (4)	0.038 (5)	0.030 (4)	0.000 (3)	0.001 (3)	0.005 (3)
C2	0.029 (4)	0.037 (5)	0.040 (4)	0.007 (4)	−0.007 (3)	0.001 (4)
C3	0.029 (4)	0.039 (5)	0.026 (4)	0.000 (3)	0.003 (3)	0.003 (3)
C4	0.036 (4)	0.033 (4)	0.023 (4)	0.010 (4)	−0.005 (3)	−0.002 (3)
C5	0.024 (4)	0.039 (5)	0.054 (5)	0.001 (3)	−0.004 (3)	0.007 (4)
C6	0.029 (4)	0.033 (5)	0.049 (5)	−0.002 (3)	0.003 (3)	0.007 (4)
C7	0.027 (4)	0.074 (6)	0.047 (5)	−0.009 (4)	−0.003 (4)	0.006 (4)
C8	0.033 (4)	0.032 (4)	0.030 (4)	−0.005 (4)	0.003 (3)	0.000 (3)
C9	0.023 (4)	0.032 (4)	0.038 (4)	0.001 (3)	0.002 (3)	−0.005 (4)
O4	0.026 (2)	0.045 (3)	0.053 (3)	0.002 (2)	0.004 (2)	0.018 (3)
O5	0.036 (3)	0.056 (4)	0.054 (4)	0.008 (3)	−0.008 (3)	0.023 (3)
O6	0.037 (3)	0.037 (3)	0.055 (3)	0.006 (2)	−0.013 (3)	0.016 (3)
N4	0.033 (3)	0.032 (3)	0.027 (3)	0.001 (3)	−0.003 (2)	0.008 (3)
N5	0.037 (3)	0.035 (4)	0.048 (4)	−0.008 (3)	−0.009 (3)	0.019 (3)
N6	0.028 (3)	0.041 (4)	0.064 (5)	−0.004 (3)	−0.007 (3)	0.011 (3)
C10	0.035 (4)	0.033 (4)	0.024 (4)	−0.001 (4)	−0.006 (3)	−0.004 (3)
C11	0.023 (3)	0.038 (4)	0.027 (4)	−0.001 (3)	−0.003 (3)	−0.001 (4)
C12	0.031 (4)	0.025 (4)	0.035 (4)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C13	0.029 (4)	0.040 (5)	0.027 (4)	0.006 (4)	−0.002 (3)	0.005 (4)
C14	0.022 (3)	0.050 (5)	0.043 (5)	0.000 (4)	−0.005 (3)	−0.001 (4)
C15	0.026 (3)	0.039 (4)	0.041 (4)	−0.006 (4)	0.001 (3)	0.012 (4)
C16	0.027 (4)	0.052 (5)	0.056 (6)	−0.008 (4)	0.000 (4)	0.005 (4)
C17	0.027 (4)	0.031 (4)	0.033 (4)	0.004 (3)	−0.007 (3)	0.004 (3)
C18	0.030 (4)	0.032 (4)	0.038 (4)	−0.004 (4)	−0.002 (3)	−0.005 (4)

O1—C3	1.365 (8)	C1—C8	1.444 (9)
O1—C7	1.418 (7)	C2—C3	1.386 (9)
O2—C4	1.373 (8)	C3—C4	1.379 (9)
O3—C9	1.232 (8)	C4—C5	1.371 (9)
O2—H2A	0.8200	C5—C6	1.383 (8)
O4—C12	1.365 (8)	C2—H2	0.9300
O4—C16	1.426 (7)	C5—H5	0.9300
O5—C13	1.374 (8)	C6—H6	0.9300
O6—C18	1.244 (8)	C7—H7C	0.9600
O5—H5A	0.8200	C7—H7A	0.9600
N1—C8	1.259 (9)	C7—H7B	0.9600
N1—N2	1.377 (8)	C8—H8	0.9300
N2—C9	1.375 (7)	C10—C11	1.409 (9)
N3—C9	1.335 (9)	C10—C15	1.384 (8)
N2—H2B	0.8600	C10—C17	1.456 (8)
N3—H3B	0.8600	C11—C12	1.388 (9)
N3—H3A	0.8600	C12—C13	1.404 (9)
N4—N5	1.375 (7)	C13—C14	1.373 (9)
N4—C17	1.282 (7)	C14—C15	1.372 (10)
N5—C18	1.353 (9)	C11—H11	0.9300
N6—C18	1.336 (9)	C14—H14	0.9300
N5—H5B	0.8600	C15—H15	0.9300
N6—H6B	0.8600	C16—H16A	0.9600
N6—H6A	0.8600	C16—H16B	0.9600
C1—C2	1.386 (9)	C16—H16C	0.9600
C1—C6	1.390 (8)	C17—H17	0.9300
C3—O1—C7	117.9 (5)	C5—C6—H6	119.00
C4—O2—H2A	109.00	H7A—C7—H7C	109.00
C12—O4—C16	117.8 (5)	H7A—C7—H7B	109.00
C13—O5—H5A	109.00	O1—C7—H7B	109.00
N2—N1—C8	116.3 (5)	O1—C7—H7C	109.00
N1—N2—C9	121.6 (5)	O1—C7—H7A	109.00
C9—N2—H2B	119.00	H7B—C7—H7C	110.00
N1—N2—H2B	119.00	C1—C8—H8	119.00
C9—N3—H3A	120.00	N1—C8—H8	118.00
H3A—N3—H3B	120.00	C11—C10—C15	119.1 (5)
C9—N3—H3B	120.00	C15—C10—C17	119.2 (5)
N5—N4—C17	114.3 (5)	C11—C10—C17	121.6 (5)
N4—N5—C18	122.7 (5)	C10—C11—C12	119.4 (5)
C18—N5—H5B	119.00	C11—C12—C13	119.5 (6)
N4—N5—H5B	119.00	O4—C12—C11	126.7 (6)
H6A—N6—H6B	120.00	O4—C12—C13	113.7 (5)
C18—N6—H6A	120.00	O5—C13—C14	119.4 (5)
C18—N6—H6B	120.00	O5—C13—C12	119.6 (5)
C2—C1—C6	118.0 (6)	C12—C13—C14	121.0 (6)
C2—C1—C8	120.9 (6)	C13—C14—C15	119.0 (6)
C6—C1—C8	121.1 (6)	C10—C15—C14	121.9 (6)
C1—C2—C3	120.7 (6)	N4—C17—C10	122.8 (5)
O1—C3—C2	126.4 (5)	N5—C18—N6	115.7 (6)
C2—C3—C4	120.0 (6)	O6—C18—N5	120.4 (6)
O1—C3—C4	113.5 (5)	O6—C18—N6	123.8 (6)
O2—C4—C5	119.0 (6)	C10—C11—H11	120.00
O2—C4—C3	120.7 (6)	C12—C11—H11	120.00
C3—C4—C5	120.4 (6)	C13—C14—H14	120.00
C4—C5—C6	119.3 (5)	C15—C14—H14	120.00
C1—C6—C5	121.6 (6)	C10—C15—H15	119.00
N1—C8—C1	123.1 (6)	C14—C15—H15	119.00
O3—C9—N2	120.3 (6)	O4—C16—H16A	110.00
N2—C9—N3	115.6 (6)	O4—C16—H16B	109.00
O3—C9—N3	124.1 (5)	O4—C16—H16C	110.00
C3—C2—H2	120.00	H16A—C16—H16B	109.00
C1—C2—H2	120.00	H16A—C16—H16C	109.00
C6—C5—H5	120.00	H16B—C16—H16C	109.00
C4—C5—H5	120.00	N4—C17—H17	119.00
C1—C6—H6	119.00	C10—C17—H17	119.00
C7—O1—C3—C2	6.5 (9)	O1—C3—C4—O2	3.3 (8)
C7—O1—C3—C4	−176.1 (6)	O1—C3—C4—C5	−177.0 (5)
C16—O4—C12—C11	2.9 (9)	C2—C3—C4—C5	0.6 (9)
C16—O4—C12—C13	−175.3 (6)	C3—C4—C5—C6	0.4 (9)
C8—N1—N2—C9	172.7 (6)	O2—C4—C5—C6	−180.0 (5)
N2—N1—C8—C1	176.9 (5)	C4—C5—C6—C1	−1.5 (9)
N1—N2—C9—N3	−2.0 (8)	C15—C10—C11—C12	−0.8 (9)
N1—N2—C9—O3	179.3 (6)	C17—C10—C11—C12	175.9 (6)
C17—N4—N5—C18	−175.8 (6)	C11—C10—C15—C14	0.5 (9)
N5—N4—C17—C10	−176.6 (5)	C17—C10—C15—C14	−176.2 (6)
N4—N5—C18—O6	−177.8 (5)	C11—C10—C17—N4	1.8 (9)
N4—N5—C18—N6	0.3 (9)	C15—C10—C17—N4	178.5 (6)
C6—C1—C8—N1	175.4 (6)	C10—C11—C12—O4	−178.3 (6)
C2—C1—C6—C5	1.5 (9)	C10—C11—C12—C13	−0.2 (9)
C6—C1—C2—C3	−0.4 (10)	O4—C12—C13—O5	0.2 (8)
C8—C1—C2—C3	−178.8 (6)	O4—C12—C13—C14	179.8 (6)
C8—C1—C6—C5	179.8 (6)	C11—C12—C13—O5	−178.2 (5)
C2—C1—C8—N1	−6.3 (10)	C11—C12—C13—C14	1.4 (9)
C1—C2—C3—C4	−0.6 (10)	O5—C13—C14—C15	178.0 (6)
C1—C2—C3—O1	176.7 (6)	C12—C13—C14—C15	−1.7 (10)
C2—C3—C4—O2	−179.0 (6)	C13—C14—C15—C10	0.7 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	2.17	2.627 (6)	115
O2—H2A···O5i	0.82	2.34	3.108 (7)	156
N2—H2B···O6ii	0.86	2.11	2.923 (7)	158
N3—H3A···O6iii	0.86	2.16	2.987 (7)	162
N3—H3B···N1	0.86	2.31	2.674 (8)	106
O5—H5A···O4	0.82	2.18	2.632 (6)	115
N5—H5B···O3iv	0.86	2.08	2.909 (7)	161
N6—H6A···O3v	0.86	2.13	2.965 (7)	164
N6—H6B···N4	0.86	2.32	2.677 (7)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	2.17	2.627 (6)	115
O2—H2A⋯O5i	0.82	2.34	3.108 (7)	156
N2—H2B⋯O6ii	0.86	2.11	2.923 (7)	158
N3—H3A⋯O6iii	0.86	2.16	2.987 (7)	162
N3—H3B⋯N1	0.86	2.31	2.674 (8)	106
O5—H5A⋯O4	0.82	2.18	2.632 (6)	115
N5—H5B⋯O3iv	0.86	2.08	2.909 (7)	161
N6—H6A⋯O3v	0.86	2.13	2.965 (7)	164
N6—H6B⋯N4	0.86	2.32	2.677 (7)	105

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