(E)-N'-(2,5-Dimethoxy-benzyl-idene)-3,4-dihydroxy-benzohydrazide monohydrate.

In the title compound, C(16)H(16)N(2)O(5)·H(2)O, the dihedral angle between the two benzene rings is 25.9 (1)°. Intra-molecular O-H⋯O and N-H⋯O hydrogen bonds are observed. In the crystal, the components are linked into a three-dimensional network by O-H⋯O and O-H⋯(O,O) hydrogen bonds.

Related literature

For related structures, see: Pu (2008 ▶); Wang et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O5·H2O

M = 334.32

Monoclinic,

a = 10.2573 (8) Å

b = 12.4199 (10) Å

c = 14.0042 (8) Å

β = 119.666 (4)°

V = 1550.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.20 × 0.18 × 0.17 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.978, T max = 0.981

7993 measured reflections

2735 independent reflections

2110 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.02

2735 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536809039300/hb5111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039300/hb5111Isup2.hkl

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

C16H16N2O5·H2O	F(000) = 704
Mr = 334.32	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2817 reflections
a = 10.2573 (8) Å	θ = 2.3–28.0°
b = 12.4199 (10) Å	µ = 0.11 mm−1
c = 14.0042 (8) Å	T = 295 K
β = 119.666 (4)°	Block, light yellow
V = 1550.2 (2) Å3	0.20 × 0.18 × 0.17 mm
Z = 4

Siemens SMART CCD diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2110 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −12→10
Tmin = 0.978, Tmax = 0.981	k = −14→14
7993 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2735 reflections	Δρmax = 0.30 e Å−3
220 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0092 (15)

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	0.29807 (12)	0.63600 (8)	0.00386 (8)	0.0415 (3)
H1	0.3478	0.6763	0.0558	0.062*
O2	0.25882 (12)	0.49266 (9)	−0.15328 (8)	0.0451 (3)
H2	0.2479	0.5582	−0.1561	0.068*
O3	0.50018 (13)	0.24912 (8)	0.30247 (8)	0.0462 (3)
O4	0.83630 (14)	0.60874 (9)	0.70864 (9)	0.0516 (3)
O5	0.84768 (13)	0.17847 (9)	0.81326 (9)	0.0554 (4)
O6	0.71520 (13)	0.60032 (9)	0.33312 (9)	0.0469 (3)
H17	0.7355	0.5747	0.2857	0.070*
H18	0.6560	0.6530	0.3021	0.070*
N1	0.56517 (14)	0.42030 (10)	0.36286 (9)	0.0374 (3)
H1A	0.5658	0.4873	0.3477	0.045*
N2	0.62828 (14)	0.38569 (10)	0.47007 (10)	0.0386 (3)
C1	0.43573 (16)	0.38751 (11)	0.16836 (11)	0.0311 (4)
C2	0.39529 (16)	0.49534 (12)	0.14219 (11)	0.0324 (4)
H2A	0.4068	0.5431	0.1970	0.039*
C3	0.33846 (15)	0.53178 (12)	0.03578 (12)	0.0306 (3)
C4	0.31715 (16)	0.45885 (12)	−0.04685 (11)	0.0328 (4)
C5	0.35509 (17)	0.35223 (13)	−0.02211 (12)	0.0380 (4)
H5	0.3408	0.3041	−0.0773	0.046*
C6	0.41477 (17)	0.31659 (12)	0.08543 (12)	0.0363 (4)
H6	0.4409	0.2445	0.1020	0.044*
C7	0.50232 (16)	0.34597 (12)	0.28220 (12)	0.0336 (4)
C8	0.69125 (17)	0.45828 (13)	0.54315 (12)	0.0378 (4)
H8	0.6879	0.5300	0.5230	0.045*
C9	0.76899 (16)	0.42735 (13)	0.65942 (11)	0.0346 (4)
C10	0.84706 (17)	0.50414 (13)	0.74194 (12)	0.0364 (4)
C11	0.92900 (17)	0.46990 (14)	0.84979 (12)	0.0410 (4)
H11	0.9825	0.5200	0.9049	0.049*
C12	0.93298 (18)	0.36251 (14)	0.87737 (12)	0.0429 (4)
H12	0.9899	0.3410	0.9503	0.051*
C13	0.85242 (18)	0.28700 (13)	0.79661 (12)	0.0396 (4)
C14	0.77166 (17)	0.32066 (13)	0.68859 (12)	0.0390 (4)
H14	0.7176	0.2702	0.6340	0.047*
C15	0.9048 (2)	0.68888 (14)	0.79085 (14)	0.0512 (5)
H15A	0.8601	0.6884	0.8370	0.077*
H15B	0.8903	0.7582	0.7567	0.077*
H15C	1.0102	0.6743	0.8344	0.077*
C16	0.9447 (2)	0.13853 (17)	0.92118 (15)	0.0683 (6)
H16A	1.0461	0.1594	0.9442	0.102*
H16B	0.9382	0.0614	0.9210	0.102*
H16C	0.9151	0.1678	0.9710	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.0508 (7)	0.0360 (6)	0.0266 (6)	0.0042 (5)	0.0106 (5)	0.0021 (5)
O2	0.0597 (8)	0.0478 (7)	0.0227 (6)	0.0049 (5)	0.0166 (6)	0.0044 (5)
O3	0.0635 (8)	0.0327 (6)	0.0257 (6)	−0.0063 (5)	0.0093 (6)	0.0017 (5)
O4	0.0685 (8)	0.0415 (7)	0.0295 (6)	−0.0086 (6)	0.0126 (6)	−0.0060 (5)
O5	0.0657 (8)	0.0467 (7)	0.0324 (7)	−0.0016 (6)	0.0079 (6)	0.0076 (5)
O6	0.0586 (8)	0.0424 (7)	0.0345 (6)	0.0024 (5)	0.0190 (6)	0.0026 (5)
N1	0.0499 (8)	0.0325 (7)	0.0176 (6)	−0.0026 (6)	0.0075 (6)	0.0025 (5)
N2	0.0463 (8)	0.0408 (8)	0.0196 (6)	−0.0029 (6)	0.0093 (6)	0.0009 (6)
C1	0.0319 (8)	0.0328 (8)	0.0222 (7)	−0.0040 (6)	0.0084 (6)	−0.0006 (6)
C2	0.0339 (8)	0.0351 (8)	0.0226 (8)	−0.0032 (6)	0.0097 (7)	−0.0039 (6)
C3	0.0280 (8)	0.0335 (8)	0.0243 (8)	0.0000 (6)	0.0084 (6)	0.0013 (6)
C4	0.0326 (8)	0.0427 (9)	0.0200 (8)	−0.0026 (7)	0.0107 (7)	0.0008 (6)
C5	0.0471 (10)	0.0385 (9)	0.0254 (8)	−0.0036 (7)	0.0156 (7)	−0.0065 (7)
C6	0.0429 (9)	0.0322 (8)	0.0277 (8)	−0.0012 (7)	0.0128 (7)	−0.0007 (7)
C7	0.0361 (9)	0.0337 (9)	0.0238 (8)	−0.0029 (6)	0.0094 (7)	−0.0008 (6)
C8	0.0433 (9)	0.0373 (9)	0.0265 (8)	−0.0001 (7)	0.0125 (7)	−0.0012 (7)
C9	0.0335 (9)	0.0432 (9)	0.0216 (8)	0.0009 (6)	0.0095 (7)	−0.0026 (6)
C10	0.0388 (9)	0.0410 (9)	0.0268 (8)	−0.0007 (7)	0.0143 (7)	−0.0034 (7)
C11	0.0438 (10)	0.0484 (10)	0.0233 (8)	−0.0048 (7)	0.0109 (7)	−0.0091 (7)
C12	0.0454 (10)	0.0542 (11)	0.0204 (8)	0.0024 (8)	0.0097 (7)	0.0005 (7)
C13	0.0425 (10)	0.0427 (10)	0.0278 (8)	0.0002 (7)	0.0130 (7)	0.0009 (7)
C14	0.0413 (9)	0.0433 (10)	0.0240 (8)	−0.0017 (7)	0.0098 (7)	−0.0041 (7)
C15	0.0569 (11)	0.0437 (10)	0.0422 (10)	−0.0060 (8)	0.0162 (9)	−0.0106 (8)
C16	0.0812 (15)	0.0597 (13)	0.0383 (11)	0.0024 (10)	0.0099 (10)	0.0188 (9)

O1—C3	1.3652 (17)	C4—C5	1.375 (2)
O1—H1	0.8200	C5—C6	1.388 (2)
O2—C4	1.3687 (16)	C5—H5	0.9300
O2—H2	0.8198	C6—H6	0.9300
O3—C7	1.2386 (17)	C8—C9	1.466 (2)
O4—C10	1.3662 (19)	C8—H8	0.9300
O4—C15	1.4173 (19)	C9—C14	1.383 (2)
O5—C13	1.3729 (19)	C9—C10	1.404 (2)
O5—C16	1.4254 (19)	C10—C11	1.383 (2)
O6—H17	0.8500	C11—C12	1.384 (2)
O6—H18	0.8508	C11—H11	0.9300
N1—C7	1.3501 (18)	C12—C13	1.384 (2)
N1—N2	1.3770 (17)	C12—H12	0.9300
N1—H1A	0.8595	C13—C14	1.382 (2)
N2—C8	1.2740 (19)	C14—H14	0.9300
C1—C6	1.387 (2)	C15—H15A	0.9600
C1—C2	1.396 (2)	C15—H15B	0.9600
C1—C7	1.482 (2)	C15—H15C	0.9600
C2—C3	1.380 (2)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.399 (2)	C16—H16C	0.9600
C3—O1—H1	109.5	C9—C8—H8	120.4
C4—O2—H2	109.4	C14—C9—C10	119.21 (14)
C10—O4—C15	117.82 (12)	C14—C9—C8	119.97 (14)
C13—O5—C16	117.19 (13)	C10—C9—C8	120.76 (14)
H17—O6—H18	106.2	O4—C10—C11	124.61 (14)
C7—N1—N2	118.09 (12)	O4—C10—C9	116.64 (13)
C7—N1—H1A	120.9	C11—C10—C9	118.75 (15)
N2—N1—H1A	121.0	C10—C11—C12	121.29 (15)
C8—N2—N1	115.64 (13)	C10—C11—H11	119.4
C6—C1—C2	119.12 (13)	C12—C11—H11	119.4
C6—C1—C7	118.53 (13)	C11—C12—C13	120.12 (14)
C2—C1—C7	122.35 (13)	C11—C12—H12	119.9
C3—C2—C1	120.64 (13)	C13—C12—H12	119.9
C3—C2—H2A	119.7	O5—C13—C14	115.51 (14)
C1—C2—H2A	119.7	O5—C13—C12	125.69 (14)
O1—C3—C2	124.19 (13)	C14—C13—C12	118.78 (15)
O1—C3—C4	116.44 (13)	C13—C14—C9	121.79 (15)
C2—C3—C4	119.36 (13)	C13—C14—H14	119.1
O2—C4—C5	119.11 (13)	C9—C14—H14	119.1
O2—C4—C3	120.48 (13)	O4—C15—H15A	109.5
C5—C4—C3	120.41 (13)	O4—C15—H15B	109.5
C4—C5—C6	119.89 (14)	H15A—C15—H15B	109.5
C4—C5—H5	120.1	O4—C15—H15C	109.5
C6—C5—H5	120.1	H15A—C15—H15C	109.5
C1—C6—C5	120.56 (14)	H15B—C15—H15C	109.5
C1—C6—H6	119.7	O5—C16—H16A	109.5
C5—C6—H6	119.7	O5—C16—H16B	109.5
O3—C7—N1	121.84 (13)	H16A—C16—H16B	109.5
O3—C7—C1	122.25 (13)	O5—C16—H16C	109.5
N1—C7—C1	115.91 (12)	H16A—C16—H16C	109.5
N2—C8—C9	119.18 (14)	H16B—C16—H16C	109.5
N2—C8—H8	120.4
C7—N1—N2—C8	177.35 (14)	N1—N2—C8—C9	−176.41 (13)
C6—C1—C2—C3	−1.5 (2)	N2—C8—C9—C14	−0.8 (2)
C7—C1—C2—C3	177.70 (13)	N2—C8—C9—C10	176.25 (15)
C1—C2—C3—O1	−179.19 (13)	C15—O4—C10—C11	−4.8 (2)
C1—C2—C3—C4	2.0 (2)	C15—O4—C10—C9	175.43 (14)
O1—C3—C4—O2	0.1 (2)	C14—C9—C10—O4	−177.86 (14)
C2—C3—C4—O2	179.00 (13)	C8—C9—C10—O4	5.1 (2)
O1—C3—C4—C5	179.83 (13)	C14—C9—C10—C11	2.4 (2)
C2—C3—C4—C5	−1.2 (2)	C8—C9—C10—C11	−174.70 (14)
O2—C4—C5—C6	179.82 (14)	O4—C10—C11—C12	179.15 (15)
C3—C4—C5—C6	0.1 (2)	C9—C10—C11—C12	−1.1 (2)
C2—C1—C6—C5	0.3 (2)	C10—C11—C12—C13	−0.9 (2)
C7—C1—C6—C5	−178.94 (14)	C16—O5—C13—C14	172.04 (16)
C4—C5—C6—C1	0.4 (2)	C16—O5—C13—C12	−6.2 (3)
N2—N1—C7—O3	0.1 (2)	C11—C12—C13—O5	179.70 (15)
N2—N1—C7—C1	179.86 (13)	C11—C12—C13—C14	1.5 (2)
C6—C1—C7—O3	−21.2 (2)	O5—C13—C14—C9	−178.57 (14)
C2—C1—C7—O3	159.56 (15)	C12—C13—C14—C9	−0.2 (2)
C6—C1—C7—N1	159.05 (14)	C10—C9—C14—C13	−1.8 (2)
C2—C1—C7—N1	−20.2 (2)	C8—C9—C14—C13	175.35 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	2.03	2.8384 (15)	168
O2—H2···O1	0.82	2.25	2.7014 (15)	115
O2—H2···O5i	0.82	2.43	3.0191 (15)	130
O6—H17···O2ii	0.85	2.06	2.9003 (15)	169
O6—H18···O3i	0.85	1.95	2.7837 (15)	165
N1—H1A···O6	0.86	2.16	2.8592 (17)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	2.03	2.8384 (15)	168
O2—H2⋯O1	0.82	2.25	2.7014 (15)	115
O2—H2⋯O5i	0.82	2.43	3.0191 (15)	130
O6—H17⋯O2ii	0.85	2.06	2.9003 (15)	169
O6—H18⋯O3i	0.85	1.95	2.7837 (15)	165
N1—H1A⋯O6	0.86	2.16	2.8592 (17)	138

Symmetry codes: (i) ; (ii) .