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

In the title compound, C(16)H(16)N(2)O(5), the dihedral angle between the two benzene rings is 4.2 (2)° and an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked into layers lying parallel to the bc plane by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶). For Schiff base compounds containing 2,5-dimethoxy­benzaldehyde, see: Wang et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O5

M = 316.31

Monoclinic,

a = 7.8600 (16) Å

b = 15.358 (3) Å

c = 12.425 (3) Å

β = 99.80 (3)°

V = 1478.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.984

7757 measured reflections

2626 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.02

2626 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 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/S160053681001130X/hb5375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001130X/hb5375Isup2.hkl

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

C16H16N2O5	F(000) = 664
Mr = 316.31	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1224 reflections
a = 7.8600 (16) Å	θ = 2.7–22.4°
b = 15.358 (3) Å	µ = 0.11 mm−1
c = 12.425 (3) Å	T = 295 K
β = 99.80 (3)°	Block, light yellow
V = 1478.0 (5) Å3	0.18 × 0.17 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.981, Tmax = 0.984	k = −17→18
7757 measured reflections	l = −13→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3
2626 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 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 > 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	0.5668 (2)	0.18995 (10)	0.34476 (11)	0.0523 (5)
H1	0.6007	0.2404	0.3438	0.078*
O2	0.2931 (2)	−0.02763 (10)	0.10807 (13)	0.0623 (5)
H2	0.3162	−0.0573	0.1635	0.093*
O3	0.6343 (2)	0.33256 (9)	0.26549 (11)	0.0477 (4)
O4	0.7730 (2)	0.58885 (10)	−0.13674 (12)	0.0569 (5)
O5	1.0792 (2)	0.67891 (10)	0.28127 (12)	0.0529 (4)
N1	0.6247 (2)	0.35121 (10)	0.08522 (13)	0.0390 (5)
H1A	0.5957	0.3331	0.0192	0.047*
N2	0.7069 (2)	0.42982 (11)	0.10809 (13)	0.0390 (5)
C1	0.5091 (3)	0.21858 (13)	0.15178 (15)	0.0329 (5)
C2	0.5058 (3)	0.16342 (13)	0.24143 (16)	0.0354 (5)
C3	0.4396 (3)	0.08035 (14)	0.22852 (16)	0.0391 (5)
H3	0.4436	0.0439	0.2887	0.047*
C4	0.3674 (3)	0.05154 (14)	0.12604 (17)	0.0421 (6)
C5	0.3657 (3)	0.10522 (15)	0.03614 (17)	0.0527 (7)
H5	0.3168	0.0857	−0.0331	0.063*
C6	0.4356 (3)	0.18663 (14)	0.04918 (16)	0.0451 (6)
H6	0.4342	0.2218	−0.0119	0.054*
C7	0.5915 (3)	0.30376 (13)	0.17057 (16)	0.0368 (5)
C8	0.7456 (3)	0.47279 (13)	0.02779 (17)	0.0386 (5)
H8	0.7160	0.4520	−0.0432	0.046*
C9	0.8368 (3)	0.55503 (13)	0.04948 (16)	0.0365 (5)
C10	0.8507 (3)	0.61312 (14)	−0.03424 (16)	0.0405 (5)
C11	0.9361 (3)	0.69144 (14)	−0.01112 (19)	0.0463 (6)
H11	0.9448	0.7304	−0.0672	0.056*
C12	1.0081 (3)	0.71168 (15)	0.09455 (18)	0.0468 (6)
H12	1.0627	0.7651	0.1097	0.056*
C13	1.0003 (3)	0.65342 (14)	0.17882 (17)	0.0405 (5)
C14	0.9151 (3)	0.57596 (14)	0.15574 (17)	0.0380 (5)
H14	0.9094	0.5366	0.2119	0.046*
C15	1.1064 (3)	0.61377 (16)	0.36363 (18)	0.0576 (7)
H15A	0.9970	0.5938	0.3785	0.086*
H15B	1.1726	0.6377	0.4290	0.086*
H15C	1.1680	0.5658	0.3390	0.086*
C16	0.8212 (4)	0.63418 (17)	−0.22690 (18)	0.0649 (8)
H16A	0.7839	0.6936	−0.2260	0.097*
H16B	0.7679	0.6070	−0.2938	0.097*
H16C	0.9445	0.6324	−0.2216	0.097*

	U11	U22	U33	U12	U13	U23
O1	0.0799 (12)	0.0477 (11)	0.0280 (8)	−0.0122 (9)	0.0054 (8)	0.0022 (7)
O2	0.0909 (13)	0.0381 (10)	0.0523 (10)	−0.0194 (9)	−0.0042 (10)	0.0057 (8)
O3	0.0727 (11)	0.0384 (9)	0.0312 (8)	−0.0072 (8)	0.0064 (7)	−0.0044 (7)
O4	0.0792 (12)	0.0540 (11)	0.0359 (9)	−0.0129 (9)	0.0045 (8)	0.0054 (7)
O5	0.0636 (11)	0.0464 (10)	0.0445 (9)	−0.0064 (8)	−0.0026 (8)	−0.0036 (8)
N1	0.0569 (12)	0.0289 (10)	0.0321 (10)	−0.0078 (9)	0.0098 (8)	−0.0038 (8)
N2	0.0502 (11)	0.0294 (10)	0.0384 (10)	−0.0049 (8)	0.0101 (9)	−0.0028 (8)
C1	0.0414 (12)	0.0287 (12)	0.0293 (11)	0.0003 (9)	0.0075 (9)	0.0018 (9)
C2	0.0394 (12)	0.0395 (13)	0.0283 (11)	0.0013 (10)	0.0082 (9)	0.0015 (10)
C3	0.0469 (13)	0.0365 (13)	0.0343 (12)	−0.0012 (10)	0.0078 (10)	0.0097 (10)
C4	0.0487 (14)	0.0327 (13)	0.0440 (13)	−0.0046 (10)	0.0058 (11)	0.0039 (10)
C5	0.0797 (18)	0.0412 (14)	0.0332 (13)	−0.0130 (13)	−0.0014 (12)	0.0002 (11)
C6	0.0657 (16)	0.0386 (13)	0.0300 (12)	−0.0073 (11)	0.0052 (11)	0.0064 (10)
C7	0.0451 (13)	0.0342 (12)	0.0315 (12)	0.0049 (10)	0.0080 (10)	0.0016 (10)
C8	0.0487 (14)	0.0341 (13)	0.0333 (12)	−0.0013 (10)	0.0076 (10)	−0.0035 (10)
C9	0.0415 (13)	0.0312 (12)	0.0378 (12)	0.0006 (10)	0.0095 (10)	0.0001 (10)
C10	0.0467 (14)	0.0383 (13)	0.0365 (12)	0.0003 (10)	0.0071 (11)	0.0011 (10)
C11	0.0558 (15)	0.0357 (13)	0.0478 (14)	−0.0033 (11)	0.0099 (12)	0.0075 (10)
C12	0.0521 (15)	0.0331 (13)	0.0550 (15)	−0.0036 (10)	0.0090 (12)	0.0000 (11)
C13	0.0420 (13)	0.0370 (13)	0.0421 (13)	−0.0014 (10)	0.0061 (10)	−0.0039 (10)
C14	0.0429 (13)	0.0329 (12)	0.0393 (12)	0.0012 (10)	0.0098 (10)	0.0036 (9)
C15	0.0654 (17)	0.0599 (17)	0.0439 (14)	−0.0057 (13)	−0.0006 (13)	0.0041 (12)
C16	0.089 (2)	0.0674 (19)	0.0395 (14)	0.0021 (16)	0.0143 (14)	0.0098 (13)

O1—C2	1.355 (2)	C5—C6	1.364 (3)
O1—H1	0.8200	C5—H5	0.9300
O2—C4	1.351 (2)	C6—H6	0.9300
O2—H2	0.8200	C8—C9	1.455 (3)
O3—C7	1.251 (2)	C8—H8	0.9300
O4—C10	1.367 (2)	C9—C10	1.389 (3)
O4—C16	1.424 (3)	C9—C14	1.396 (3)
O5—C13	1.375 (2)	C10—C11	1.384 (3)
O5—C15	1.421 (3)	C11—C12	1.374 (3)
N1—C7	1.348 (2)	C11—H11	0.9300
N1—N2	1.376 (2)	C12—C13	1.387 (3)
N1—H1A	0.8600	C12—H12	0.9300
N2—C8	1.275 (2)	C13—C14	1.371 (3)
C1—C6	1.396 (3)	C14—H14	0.9300
C1—C2	1.403 (3)	C15—H15A	0.9600
C1—C7	1.461 (3)	C15—H15B	0.9600
C2—C3	1.377 (3)	C15—H15C	0.9600
C3—C4	1.376 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.387 (3)	C16—H16C	0.9600
C2—O1—H1	109.5	C9—C8—H8	120.7
C4—O2—H2	109.5	C10—C9—C14	118.8 (2)
C10—O4—C16	117.56 (18)	C10—C9—C8	121.21 (19)
C13—O5—C15	117.08 (17)	C14—C9—C8	119.95 (19)
C7—N1—N2	117.31 (17)	O4—C10—C11	123.68 (19)
C7—N1—H1A	121.3	O4—C10—C9	116.29 (19)
N2—N1—H1A	121.3	C11—C10—C9	120.0 (2)
C8—N2—N1	117.29 (17)	C12—C11—C10	120.1 (2)
C6—C1—C2	116.88 (19)	C12—C11—H11	119.9
C6—C1—C7	124.33 (18)	C10—C11—H11	119.9
C2—C1—C7	118.77 (18)	C11—C12—C13	120.8 (2)
O1—C2—C3	117.07 (18)	C11—C12—H12	119.6
O1—C2—C1	121.30 (19)	C13—C12—H12	119.6
C3—C2—C1	121.64 (19)	C14—C13—O5	124.6 (2)
C4—C3—C2	119.61 (19)	C14—C13—C12	119.0 (2)
C4—C3—H3	120.2	O5—C13—C12	116.4 (2)
C2—C3—H3	120.2	C13—C14—C9	121.2 (2)
O2—C4—C3	122.76 (19)	C13—C14—H14	119.4
O2—C4—C5	117.22 (19)	C9—C14—H14	119.4
C3—C4—C5	120.0 (2)	O5—C15—H15A	109.5
C6—C5—C4	120.1 (2)	O5—C15—H15B	109.5
C6—C5—H5	120.0	H15A—C15—H15B	109.5
C4—C5—H5	120.0	O5—C15—H15C	109.5
C5—C6—C1	121.75 (19)	H15A—C15—H15C	109.5
C5—C6—H6	119.1	H15B—C15—H15C	109.5
C1—C6—H6	119.1	O4—C16—H16A	109.5
O3—C7—N1	119.56 (19)	O4—C16—H16B	109.5
O3—C7—C1	120.54 (18)	H16A—C16—H16B	109.5
N1—C7—C1	119.89 (18)	O4—C16—H16C	109.5
N2—C8—C9	118.67 (19)	H16A—C16—H16C	109.5
N2—C8—H8	120.7	H16B—C16—H16C	109.5
C7—N1—N2—C8	176.80 (19)	N1—N2—C8—C9	−178.34 (17)
C6—C1—C2—O1	−176.99 (19)	N2—C8—C9—C10	−166.4 (2)
C7—C1—C2—O1	4.5 (3)	N2—C8—C9—C14	14.8 (3)
C6—C1—C2—C3	2.6 (3)	C16—O4—C10—C11	17.6 (3)
C7—C1—C2—C3	−175.98 (19)	C16—O4—C10—C9	−163.9 (2)
O1—C2—C3—C4	176.54 (19)	C14—C9—C10—O4	179.36 (18)
C1—C2—C3—C4	−3.0 (3)	C8—C9—C10—O4	0.6 (3)
C2—C3—C4—O2	−176.9 (2)	C14—C9—C10—C11	−2.1 (3)
C2—C3—C4—C5	1.7 (3)	C8—C9—C10—C11	179.09 (19)
O2—C4—C5—C6	178.7 (2)	O4—C10—C11—C12	178.8 (2)
C3—C4—C5—C6	0.0 (4)	C9—C10—C11—C12	0.4 (3)
C4—C5—C6—C1	−0.4 (4)	C10—C11—C12—C13	1.7 (3)
C2—C1—C6—C5	−0.8 (3)	C15—O5—C13—C14	14.2 (3)
C7—C1—C6—C5	177.6 (2)	C15—O5—C13—C12	−166.4 (2)
N2—N1—C7—O3	0.6 (3)	C11—C12—C13—C14	−1.9 (3)
N2—N1—C7—C1	−178.22 (17)	C11—C12—C13—O5	178.70 (19)
C6—C1—C7—O3	170.6 (2)	O5—C13—C14—C9	179.43 (19)
C2—C1—C7—O3	−11.0 (3)	C12—C13—C14—C9	0.0 (3)
C6—C1—C7—N1	−10.6 (3)	C10—C9—C14—C13	1.9 (3)
C2—C1—C7—N1	167.86 (19)	C8—C9—C14—C13	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.76	2.495 (2)	148
O2—H2···O3i	0.82	1.92	2.664 (2)	151
N1—H1A···O1ii	0.86	2.17	3.012 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.76	2.495 (2)	148
O2—H2⋯O3i	0.82	1.92	2.664 (2)	151
N1—H1A⋯O1ii	0.86	2.17	3.012 (2)	166

Symmetry codes: (i) ; (ii) .