2,4-Dihydr-oxy-N'-(3,4,5-trimethoxy-benzyl-idene)benzohydrazide.

In the title compound, C(17)H(18)N(2)O(6), the mol-ecule is slightly twisted, with a dihedral angle of 18.1 (2)° between the two benzene rings. In the crystal structure, mol-ecules are linked into a network by inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond is also present.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For the crystal structures of some Schiff bases and their complexes, see: Diao (2007 ▶); Diao et al. (2007 ▶, 2008 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C17H18N2O6

M = 346.33

Orthorhombic,

a = 14.601 (1) Å

b = 11.030 (2) Å

c = 20.006 (2) Å

V = 3222.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.978, T max = 0.978

18590 measured reflections

3520 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.148

S = 1.03

3520 reflections

234 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035764/wn2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035764/wn2345Isup2.hkl

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

C17H18N2O6	F(000) = 1456
Mr = 346.33	Dx = 1.428 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2734 reflections
a = 14.601 (1) Å	θ = 2.5–26.0°
b = 11.030 (2) Å	µ = 0.11 mm−1
c = 20.006 (2) Å	T = 298 K
V = 3222.0 (7) Å3	Block, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3520 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
Tmin = 0.978, Tmax = 0.978	k = −12→14
18590 measured reflections	l = −20→25

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.9796P] where P = (Fo2 + 2Fc2)/3
3520 reflections	(Δ/σ)max = 0.001
234 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

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
N1	−0.07006 (12)	0.46657 (17)	0.36310 (9)	0.0409 (5)
N2	0.00500 (12)	0.44220 (16)	0.40282 (9)	0.0410 (4)
O1	0.01502 (10)	0.60011 (16)	0.30628 (8)	0.0528 (5)
O2	−0.04899 (12)	0.72863 (18)	0.21335 (9)	0.0650 (5)
H2	−0.0112	0.7057	0.2409	0.097*
O3	−0.33269 (11)	0.63390 (17)	0.12189 (8)	0.0555 (5)
H3	−0.3814	0.6018	0.1322	0.083*
O4	0.12167 (11)	0.13843 (16)	0.63808 (9)	0.0584 (5)
O5	0.28830 (10)	0.21803 (14)	0.60976 (8)	0.0474 (4)
O6	0.31779 (11)	0.37901 (16)	0.51322 (9)	0.0579 (5)
C1	−0.21013 (15)	0.4894 (2)	0.25893 (12)	0.0420 (5)
H1	−0.2169	0.4251	0.2886	0.050*
C2	−0.13151 (14)	0.56173 (19)	0.26278 (11)	0.0384 (5)
C3	−0.12280 (15)	0.6558 (2)	0.21550 (11)	0.0431 (5)
C4	−0.19085 (16)	0.6778 (2)	0.16936 (12)	0.0465 (6)
H4	−0.1843	0.7408	0.1388	0.056*
C5	−0.26856 (15)	0.6071 (2)	0.16830 (11)	0.0418 (5)
C6	−0.27758 (15)	0.5110 (2)	0.21243 (11)	0.0421 (5)
H6	−0.3290	0.4613	0.2106	0.050*
C7	−0.05838 (14)	0.54391 (19)	0.31173 (11)	0.0396 (5)
C8	−0.00724 (15)	0.3683 (2)	0.45107 (11)	0.0423 (5)
H8	−0.0652	0.3366	0.4593	0.051*
C9	0.07007 (15)	0.33347 (19)	0.49349 (11)	0.0402 (5)
C10	0.15711 (15)	0.3793 (2)	0.48163 (11)	0.0435 (5)
H10	0.1665	0.4351	0.4475	0.052*
C11	0.22944 (15)	0.3418 (2)	0.52056 (12)	0.0437 (6)
C12	0.21532 (15)	0.2592 (2)	0.57258 (11)	0.0411 (5)
C13	0.12835 (16)	0.2157 (2)	0.58524 (11)	0.0428 (5)
C14	0.05539 (15)	0.2521 (2)	0.54515 (11)	0.0428 (5)
H14	−0.0031	0.2219	0.5530	0.051*
C15	0.33483 (18)	0.4696 (3)	0.46434 (14)	0.0652 (8)
H15A	0.3242	0.4367	0.4206	0.098*
H15B	0.3973	0.4962	0.4677	0.098*
H15C	0.2946	0.5371	0.4717	0.098*
C16	0.3270 (2)	0.3053 (2)	0.65403 (14)	0.0655 (8)
H16A	0.3195	0.3850	0.6355	0.098*
H16B	0.3910	0.2887	0.6599	0.098*
H16C	0.2966	0.3010	0.6965	0.098*
C17	0.03536 (19)	0.0858 (3)	0.65186 (14)	0.0646 (8)
H17A	−0.0098	0.1486	0.6560	0.097*
H17B	0.0387	0.0408	0.6929	0.097*
H17C	0.0186	0.0323	0.6160	0.097*
H1A	−0.1231 (10)	0.4289 (19)	0.3709 (11)	0.050*

	U11	U22	U33	U12	U13	U23
N1	0.0320 (10)	0.0498 (11)	0.0407 (11)	−0.0008 (8)	−0.0063 (8)	0.0046 (8)
N2	0.0349 (10)	0.0496 (10)	0.0385 (11)	0.0046 (8)	−0.0062 (8)	−0.0037 (9)
O1	0.0353 (9)	0.0687 (11)	0.0544 (11)	−0.0083 (8)	−0.0044 (8)	0.0092 (8)
O2	0.0514 (11)	0.0832 (13)	0.0603 (12)	−0.0237 (10)	−0.0062 (8)	0.0223 (10)
O3	0.0411 (9)	0.0797 (12)	0.0457 (10)	−0.0056 (9)	−0.0069 (8)	0.0135 (9)
O4	0.0475 (10)	0.0716 (11)	0.0561 (11)	−0.0065 (8)	−0.0100 (8)	0.0231 (9)
O5	0.0397 (9)	0.0548 (9)	0.0477 (10)	0.0062 (7)	−0.0115 (7)	−0.0020 (8)
O6	0.0359 (9)	0.0830 (12)	0.0548 (11)	−0.0034 (8)	−0.0009 (8)	0.0142 (9)
C1	0.0383 (12)	0.0432 (12)	0.0445 (13)	−0.0004 (9)	0.0003 (10)	0.0051 (10)
C2	0.0321 (11)	0.0461 (12)	0.0371 (12)	0.0001 (9)	0.0016 (9)	0.0015 (10)
C3	0.0340 (12)	0.0543 (13)	0.0411 (13)	−0.0075 (10)	0.0014 (10)	0.0021 (11)
C4	0.0445 (14)	0.0559 (14)	0.0391 (13)	−0.0046 (11)	0.0008 (10)	0.0104 (11)
C5	0.0347 (12)	0.0586 (14)	0.0320 (12)	0.0022 (10)	−0.0010 (9)	−0.0001 (10)
C6	0.0349 (12)	0.0469 (12)	0.0444 (13)	−0.0044 (10)	−0.0017 (10)	0.0005 (11)
C7	0.0305 (11)	0.0465 (12)	0.0417 (13)	−0.0004 (9)	0.0013 (9)	−0.0037 (10)
C8	0.0350 (12)	0.0497 (13)	0.0423 (13)	−0.0002 (10)	−0.0053 (10)	−0.0020 (11)
C9	0.0368 (12)	0.0463 (12)	0.0374 (13)	0.0027 (9)	−0.0051 (10)	−0.0036 (10)
C10	0.0419 (13)	0.0529 (13)	0.0356 (12)	0.0032 (10)	−0.0025 (10)	0.0037 (10)
C11	0.0326 (12)	0.0558 (14)	0.0427 (13)	0.0010 (10)	0.0004 (10)	−0.0020 (11)
C12	0.0354 (12)	0.0479 (12)	0.0399 (13)	0.0062 (10)	−0.0062 (10)	−0.0028 (10)
C13	0.0437 (13)	0.0464 (12)	0.0382 (13)	0.0023 (10)	−0.0032 (10)	0.0016 (10)
C14	0.0338 (12)	0.0519 (13)	0.0428 (13)	−0.0014 (10)	−0.0033 (10)	−0.0012 (11)
C15	0.0477 (16)	0.0815 (19)	0.0664 (18)	−0.0079 (13)	0.0057 (14)	0.0125 (15)
C16	0.0667 (18)	0.0671 (17)	0.0629 (18)	0.0099 (14)	−0.0232 (15)	−0.0177 (14)
C17	0.0556 (16)	0.0703 (17)	0.0678 (18)	−0.0114 (14)	−0.0058 (14)	0.0237 (14)

N1—C7	1.346 (3)	C4—H4	0.9300
N1—N2	1.380 (2)	C5—C6	1.386 (3)
N1—H1A	0.893 (10)	C6—H6	0.9300
N2—C8	1.276 (3)	C8—C9	1.464 (3)
O1—C7	1.243 (2)	C8—H8	0.9300
O2—C3	1.345 (3)	C9—C14	1.385 (3)
O2—H2	0.8200	C9—C10	1.388 (3)
O3—C5	1.351 (3)	C10—C11	1.376 (3)
O3—H3	0.8200	C10—H10	0.9300
O4—C13	1.362 (3)	C11—C12	1.399 (3)
O4—C17	1.415 (3)	C12—C13	1.381 (3)
O5—C12	1.376 (2)	C13—C14	1.393 (3)
O5—C16	1.425 (3)	C14—H14	0.9300
O6—C11	1.362 (3)	C15—H15A	0.9600
O6—C15	1.420 (3)	C15—H15B	0.9600
C1—C6	1.375 (3)	C15—H15C	0.9600
C1—C2	1.400 (3)	C16—H16A	0.9600
C1—H1	0.9300	C16—H16B	0.9600
C2—C3	1.410 (3)	C16—H16C	0.9600
C2—C7	1.462 (3)	C17—H17A	0.9600
C3—C4	1.378 (3)	C17—H17B	0.9600
C4—C5	1.377 (3)	C17—H17C	0.9600
C7—N1—N2	117.54 (17)	C10—C9—C8	120.8 (2)
C7—N1—H1A	122.6 (15)	C11—C10—C9	119.8 (2)
N2—N1—H1A	119.8 (15)	C11—C10—H10	120.1
C8—N2—N1	116.67 (18)	C9—C10—H10	120.1
C3—O2—H2	109.5	O6—C11—C10	125.2 (2)
C5—O3—H3	109.5	O6—C11—C12	114.60 (19)
C13—O4—C17	118.17 (18)	C10—C11—C12	120.2 (2)
C12—O5—C16	114.84 (18)	O5—C12—C13	119.9 (2)
C11—O6—C15	116.89 (19)	O5—C12—C11	120.2 (2)
C6—C1—C2	121.7 (2)	C13—C12—C11	119.9 (2)
C6—C1—H1	119.1	O4—C13—C12	115.19 (19)
C2—C1—H1	119.1	O4—C13—C14	124.9 (2)
C1—C2—C3	117.1 (2)	C12—C13—C14	119.9 (2)
C1—C2—C7	124.0 (2)	C9—C14—C13	119.9 (2)
C3—C2—C7	118.85 (19)	C9—C14—H14	120.1
O2—C3—C4	116.8 (2)	C13—C14—H14	120.1
O2—C3—C2	122.2 (2)	O6—C15—H15A	109.5
C4—C3—C2	121.0 (2)	O6—C15—H15B	109.5
C5—C4—C3	120.3 (2)	H15A—C15—H15B	109.5
C5—C4—H4	119.8	O6—C15—H15C	109.5
C3—C4—H4	119.8	H15A—C15—H15C	109.5
O3—C5—C4	117.2 (2)	H15B—C15—H15C	109.5
O3—C5—C6	122.6 (2)	O5—C16—H16A	109.5
C4—C5—C6	120.1 (2)	O5—C16—H16B	109.5
C1—C6—C5	119.7 (2)	H16A—C16—H16B	109.5
C1—C6—H6	120.2	O5—C16—H16C	109.5
C5—C6—H6	120.2	H16A—C16—H16C	109.5
O1—C7—N1	119.5 (2)	H16B—C16—H16C	109.5
O1—C7—C2	120.3 (2)	O4—C17—H17A	109.5
N1—C7—C2	120.25 (19)	O4—C17—H17B	109.5
N2—C8—C9	119.9 (2)	H17A—C17—H17B	109.5
N2—C8—H8	120.1	O4—C17—H17C	109.5
C9—C8—H8	120.1	H17A—C17—H17C	109.5
C14—C9—C10	120.3 (2)	H17B—C17—H17C	109.5
C14—C9—C8	118.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.89 (1)	2.11 (1)	2.953 (2)	157 (2)
O3—H3···N2ii	0.82	2.52	3.214 (3)	143
O3—H3···O1ii	0.82	1.95	2.674 (2)	147
O2—H2···O1	0.82	1.79	2.518 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.893 (10)	2.109 (13)	2.953 (2)	157 (2)
O3—H3⋯N2ii	0.82	2.52	3.214 (3)	143
O3—H3⋯O1ii	0.82	1.95	2.674 (2)	147
O2—H2⋯O1	0.82	1.79	2.518 (2)	147

Symmetry codes: (i) ; (ii) .