(E)-4-Amino-N'-(2-hy-droxy-5-meth-oxy-benzyl-idene)benzohydrazide monohydrate.

In the title compound, C(15)H(15)N(3)O(3)·H(2)O, the hydazide Schiff base mol-ecule shows an E conformation around the C=N bond. An intra-molecular O-H⋯N hydrogen bond makes an S(6) ring motif. The dihedral angle between the substituted phenyl rings is 23.40 (11)°. The water mol-ecule mediates linking of neighbouring mol-ecules through O-H⋯(O,O) hydrogen bonds into infinite chains along the a axis, which are further connected together through N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001). C-H⋯O inter-actions aso occur.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For 4-amino­benzohydrazide-derived Schiff base structures, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶); Kargar et al. (2012 ▶).

Experimental

Crystal data

C15H15N3O3·H2O

M = 303.32

Monoclinic,

a = 4.7376 (5) Å

b = 13.270 (2) Å

c = 11.7265 (16) Å

β = 98.459 (4)°

V = 729.18 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.982

6511 measured reflections

1679 independent reflections

1433 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.03

1679 reflections

200 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026633/bq2366sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026633/bq2366Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026633/bq2366Isup3.cml

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

C15H15N3O3·H2O	F(000) = 320
Mr = 303.32	Dx = 1.381 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 873 reflections
a = 4.7376 (5) Å	θ = 2.5–28.5°
b = 13.270 (2) Å	µ = 0.10 mm−1
c = 11.7265 (16) Å	T = 291 K
β = 98.459 (4)°	Prism, white
V = 729.18 (17) Å3	0.28 × 0.20 × 0.18 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	1679 independent reflections
Radiation source: fine-focus sealed tube	1433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→6
Tmin = 0.972, Tmax = 0.982	k = −17→17
6511 measured reflections	l = −15→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.0579P] where P = (Fo2 + 2Fc2)/3
1679 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.2636 (4)	0.77661 (14)	−0.05541 (17)	0.0508 (5)
O2	−0.2127 (4)	0.80740 (14)	0.21112 (17)	0.0525 (5)
H2	−0.1070	0.7823	0.1570	0.079*
O3	−0.7483 (4)	0.51216 (16)	0.43124 (16)	0.0576 (6)
O1W	0.2220 (4)	0.39655 (14)	0.06445 (17)	0.0554 (5)
H1W1	0.3915	0.3618	0.0655	0.083*
H2W1	0.0724	0.3628	0.0602	0.083*
N1	0.9460 (5)	0.49031 (19)	−0.3593 (2)	0.0563 (6)
H1N1	1.0085	0.5262	−0.4186	0.084*
H2N1	1.0325	0.4284	−0.3229	0.084*
N2	0.1583 (4)	0.62403 (16)	0.01294 (17)	0.0385 (5)
H2N	0.1776	0.5530	0.0164	0.046*
N3	−0.0003 (4)	0.66404 (16)	0.09130 (17)	0.0380 (5)
C1	0.4541 (4)	0.6311 (2)	−0.1357 (2)	0.0343 (5)
C2	0.5460 (5)	0.53219 (18)	−0.1196 (2)	0.0389 (6)
H2A	0.4945	0.4956	−0.0582	0.047*
C3	0.7107 (5)	0.48700 (19)	−0.1917 (2)	0.0424 (6)
H3A	0.7718	0.4209	−0.1778	0.051*
C4	0.7876 (5)	0.5391 (2)	−0.2859 (2)	0.0409 (6)
C5	0.6937 (6)	0.6372 (2)	−0.3037 (2)	0.0470 (6)
H5A	0.7407	0.6732	−0.3664	0.056*
C6	0.5309 (5)	0.6824 (2)	−0.2298 (2)	0.0439 (6)
H6A	0.4714	0.7487	−0.2432	0.053*
C7	0.2861 (5)	0.68406 (19)	−0.0575 (2)	0.0359 (5)
C8	−0.1204 (5)	0.59925 (19)	0.1497 (2)	0.0388 (6)
H8A	−0.0947	0.5309	0.1370	0.047*
C9	−0.2965 (5)	0.6304 (2)	0.2356 (2)	0.0357 (5)
C10	−0.3358 (5)	0.7308 (2)	0.2623 (2)	0.0386 (5)
C11	−0.5064 (5)	0.7548 (2)	0.3461 (2)	0.0462 (7)
H11A	−0.5315	0.8219	0.3651	0.055*
C12	−0.6366 (6)	0.6808 (2)	0.4005 (2)	0.0459 (7)
H12A	−0.7489	0.6981	0.4562	0.055*
C13	−0.6028 (5)	0.5804 (2)	0.3732 (2)	0.0421 (6)
C14	−0.4317 (5)	0.5551 (2)	0.2919 (2)	0.0404 (6)
H14A	−0.4058	0.4877	0.2743	0.049*
C15	−0.7400 (8)	0.4101 (3)	0.3976 (3)	0.0687 (9)
H15A	−0.8667	0.3713	0.4372	0.103*
H15B	−0.5491	0.3848	0.4169	0.103*
H15C	−0.7986	0.4047	0.3159	0.103*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (10)	0.0383 (11)	0.0708 (13)	0.0017 (8)	0.0294 (9)	−0.0014 (9)
O2	0.0604 (11)	0.0439 (11)	0.0593 (12)	−0.0043 (9)	0.0290 (10)	−0.0038 (9)
O3	0.0680 (13)	0.0610 (13)	0.0512 (12)	−0.0032 (10)	0.0335 (10)	0.0064 (9)
O1W	0.0532 (11)	0.0398 (10)	0.0783 (14)	−0.0022 (9)	0.0271 (10)	0.0019 (9)
N1	0.0682 (15)	0.0580 (15)	0.0502 (13)	0.0072 (13)	0.0343 (12)	−0.0005 (12)
N2	0.0362 (10)	0.0410 (11)	0.0421 (11)	0.0000 (10)	0.0183 (9)	−0.0052 (10)
N3	0.0316 (10)	0.0471 (12)	0.0378 (11)	0.0012 (9)	0.0138 (8)	−0.0056 (9)
C1	0.0305 (11)	0.0378 (13)	0.0363 (12)	−0.0033 (10)	0.0101 (9)	−0.0029 (10)
C2	0.0437 (13)	0.0367 (13)	0.0406 (13)	−0.0007 (11)	0.0199 (11)	0.0026 (10)
C3	0.0483 (14)	0.0364 (14)	0.0460 (14)	0.0041 (11)	0.0182 (12)	0.0000 (11)
C4	0.0390 (13)	0.0484 (15)	0.0385 (13)	−0.0013 (11)	0.0161 (11)	−0.0050 (11)
C5	0.0570 (15)	0.0480 (16)	0.0407 (14)	−0.0011 (13)	0.0227 (12)	0.0104 (12)
C6	0.0526 (15)	0.0372 (14)	0.0452 (14)	0.0025 (12)	0.0184 (12)	0.0028 (11)
C7	0.0282 (11)	0.0386 (14)	0.0421 (14)	−0.0011 (10)	0.0093 (10)	−0.0026 (11)
C8	0.0372 (12)	0.0430 (14)	0.0386 (13)	0.0039 (10)	0.0135 (10)	−0.0034 (10)
C9	0.0293 (11)	0.0459 (14)	0.0331 (12)	0.0025 (11)	0.0084 (9)	−0.0032 (11)
C10	0.0365 (13)	0.0452 (14)	0.0356 (12)	0.0012 (11)	0.0103 (10)	−0.0003 (11)
C11	0.0495 (15)	0.0501 (17)	0.0412 (14)	0.0055 (12)	0.0143 (12)	−0.0084 (12)
C12	0.0466 (14)	0.0589 (18)	0.0353 (13)	0.0068 (13)	0.0166 (11)	−0.0042 (13)
C13	0.0413 (14)	0.0544 (16)	0.0326 (13)	0.0031 (12)	0.0118 (11)	0.0027 (12)
C14	0.0422 (13)	0.0427 (14)	0.0391 (13)	0.0072 (11)	0.0148 (11)	−0.0014 (11)
C15	0.091 (2)	0.0530 (19)	0.070 (2)	−0.0032 (17)	0.0381 (19)	0.0106 (16)

O1—C7	1.233 (3)	C3—H3A	0.9300
O2—C10	1.355 (3)	C4—C5	1.383 (4)
O2—H2	0.9261	C5—C6	1.379 (3)
O3—C13	1.377 (3)	C5—H5A	0.9300
O3—C15	1.413 (4)	C6—H6A	0.9300
O1W—H1W1	0.9247	C8—C9	1.459 (3)
O1W—H2W1	0.8339	C8—H8A	0.9300
N1—C4	1.383 (3)	C9—C10	1.387 (4)
N1—H1N1	0.9272	C9—C14	1.403 (4)
N1—H2N1	0.9864	C10—C11	1.398 (3)
N2—C7	1.353 (3)	C11—C12	1.366 (4)
N2—N3	1.376 (3)	C11—H11A	0.9300
N2—H2N	0.9473	C12—C13	1.386 (4)
N3—C8	1.284 (3)	C12—H12A	0.9300
C1—C2	1.387 (3)	C13—C14	1.381 (3)
C1—C6	1.390 (3)	C14—H14A	0.9300
C1—C7	1.478 (3)	C15—H15A	0.9600
C2—C3	1.370 (3)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.396 (3)
C10—O2—H2	110.2	O1—C7—C1	122.8 (2)
C13—O3—C15	117.1 (2)	N2—C7—C1	115.4 (2)
H1W1—O1W—H2W1	117.5	N3—C8—C9	121.5 (2)
C4—N1—H1N1	119.3	N3—C8—H8A	119.3
C4—N1—H2N1	110.4	C9—C8—H8A	119.3
H1N1—N1—H2N1	126.4	C10—C9—C14	119.5 (2)
C7—N2—N3	121.2 (2)	C10—C9—C8	122.5 (2)
C7—N2—H2N	124.2	C14—C9—C8	118.0 (2)
N3—N2—H2N	114.5	O2—C10—C9	122.7 (2)
C8—N3—N2	115.2 (2)	O2—C10—C11	118.1 (2)
C2—C1—C6	117.3 (2)	C9—C10—C11	119.2 (2)
C2—C1—C7	123.5 (2)	C12—C11—C10	120.8 (3)
C6—C1—C7	119.2 (2)	C12—C11—H11A	119.6
C3—C2—C1	121.7 (2)	C10—C11—H11A	119.6
C3—C2—H2A	119.1	C11—C12—C13	120.6 (2)
C1—C2—H2A	119.1	C11—C12—H12A	119.7
C2—C3—C4	120.7 (2)	C13—C12—H12A	119.7
C2—C3—H3A	119.7	O3—C13—C14	124.7 (3)
C4—C3—H3A	119.7	O3—C13—C12	115.8 (2)
C5—C4—N1	122.6 (2)	C14—C13—C12	119.5 (2)
C5—C4—C3	118.1 (2)	C13—C14—C9	120.5 (2)
N1—C4—C3	119.3 (2)	C13—C14—H14A	119.8
C6—C5—C4	120.8 (2)	C9—C14—H14A	119.8
C6—C5—H5A	119.6	O3—C15—H15A	109.5
C4—C5—H5A	119.6	O3—C15—H15B	109.5
C5—C6—C1	121.5 (2)	H15A—C15—H15B	109.5
C5—C6—H6A	119.3	O3—C15—H15C	109.5
C1—C6—H6A	119.3	H15A—C15—H15C	109.5
O1—C7—N2	121.8 (2)	H15B—C15—H15C	109.5
C7—N2—N3—C8	177.2 (2)	N3—C8—C9—C10	−2.5 (3)
C6—C1—C2—C3	1.3 (3)	N3—C8—C9—C14	177.0 (2)
C7—C1—C2—C3	−177.5 (2)	C14—C9—C10—O2	−179.8 (2)
C1—C2—C3—C4	−1.2 (4)	C8—C9—C10—O2	−0.3 (4)
C2—C3—C4—C5	0.2 (4)	C14—C9—C10—C11	0.9 (3)
C2—C3—C4—N1	−177.9 (2)	C8—C9—C10—C11	−179.6 (2)
N1—C4—C5—C6	178.6 (3)	O2—C10—C11—C12	179.8 (2)
C3—C4—C5—C6	0.6 (4)	C9—C10—C11—C12	−0.8 (4)
C4—C5—C6—C1	−0.5 (4)	C10—C11—C12—C13	−0.2 (4)
C2—C1—C6—C5	−0.4 (4)	C15—O3—C13—C14	−5.6 (4)
C7—C1—C6—C5	178.4 (2)	C15—O3—C13—C12	174.2 (3)
N3—N2—C7—O1	−0.8 (4)	C11—C12—C13—O3	−178.6 (2)
N3—N2—C7—C1	178.87 (19)	C11—C12—C13—C14	1.2 (4)
C2—C1—C7—O1	162.1 (2)	O3—C13—C14—C9	178.7 (2)
C6—C1—C7—O1	−16.6 (4)	C12—C13—C14—C9	−1.1 (4)
C2—C1—C7—N2	−17.6 (3)	C10—C9—C14—C13	0.0 (3)
C6—C1—C7—N2	163.7 (2)	C8—C9—C14—C13	−179.4 (2)
N2—N3—C8—C9	−179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1i	0.92	2.00	2.926 (3)	174
O2—H2···N3	0.93	1.85	2.650 (3)	143
O1W—H2W1···O1ii	0.83	1.95	2.787 (3)	176
N2—H2N···O1W	0.95	2.15	3.084 (3)	167
N1—H1N1···O3iii	0.93	2.25	3.043 (3)	143
N1—H2N1···O2i	0.99	2.17	3.141 (3)	169
C2—H2A···O1W	0.93	2.45	3.351 (3)	163
C8—H8A···O1W	0.93	2.56	3.368 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1i	0.92	2.00	2.926 (3)	174
O2—H2⋯N3	0.93	1.85	2.650 (3)	143
O1W—H2W1⋯O1ii	0.83	1.95	2.787 (3)	176
N2—H2N⋯O1W	0.95	2.15	3.084 (3)	167
N1—H1N1⋯O3iii	0.93	2.25	3.043 (3)	143
N1—H2N1⋯O2i	0.99	2.17	3.141 (3)	169
C2—H2A⋯O1W	0.93	2.45	3.351 (3)	163
C8—H8A⋯O1W	0.93	2.56	3.368 (3)	146

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