N'-(2,3-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 8.5 (3)° and the mol-ecule adopts an E configuration with respect to the C=N bond. There is an intra-molecular N-H⋯O hydrogen bond in the mol-ecule, which generates an S(6) ring. In the crystal, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related structures and background information, see: Han & Zhao (2010a ▶,b ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O5

M = 316.31

Monoclinic,

a = 24.918 (4) Å

b = 5.0291 (8) Å

c = 13.075 (2) Å

β = 118.994 (2)°

V = 1433.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.978, T max = 0.980

3934 measured reflections

1549 independent reflections

1247 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 0.78

1549 reflections

215 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536810012134/hb5385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012134/hb5385Isup2.hkl

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

C16H16N2O5	F(000) = 664
Mr = 316.31	Dx = 1.466 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1397 reflections
a = 24.918 (4) Å	θ = 2.7–25.0°
b = 5.0291 (8) Å	µ = 0.11 mm−1
c = 13.075 (2) Å	T = 298 K
β = 118.994 (2)°	Block, colourless
V = 1433.1 (4) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1549 independent reflections
Radiation source: fine-focus sealed tube	1247 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −23→31
Tmin = 0.978, Tmax = 0.980	k = −6→6
3934 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 0.78	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.0824P] where P = (Fo2 + 2Fc2)/3
1549 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.15 e Å−3
3 restraints	Δρmin = −0.15 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
N1	0.34984 (10)	0.3854 (5)	0.19993 (19)	0.0380 (5)
N2	0.32187 (10)	0.2191 (4)	0.24411 (19)	0.0393 (5)
O1	0.35804 (9)	0.5925 (4)	0.02075 (15)	0.0441 (5)
H1	0.3604	0.5886	−0.0396	0.066*
O2	0.49643 (9)	1.3145 (4)	0.09920 (16)	0.0456 (5)
H2	0.4745	1.3395	0.0289	0.068*
O3	0.41233 (10)	0.5503 (4)	0.37839 (17)	0.0460 (5)
O4	0.18657 (10)	−0.2434 (4)	0.00073 (18)	0.0474 (5)
O5	0.11485 (10)	−0.5565 (4)	0.05383 (18)	0.0526 (6)
C1	0.42086 (11)	0.7354 (5)	0.2189 (2)	0.0317 (5)
C2	0.40165 (11)	0.7604 (5)	0.0990 (2)	0.0310 (5)
C3	0.42595 (12)	0.9539 (5)	0.0580 (2)	0.0348 (5)
H3	0.4117	0.9707	−0.0219	0.042*
C4	0.47143 (12)	1.1230 (5)	0.1358 (2)	0.0339 (6)
C5	0.49350 (13)	1.0928 (5)	0.2551 (2)	0.0409 (6)
H5	0.5254	1.1995	0.3082	0.049*
C6	0.46786 (12)	0.9044 (5)	0.2941 (2)	0.0381 (6)
H6	0.4825	0.8886	0.3741	0.046*
C7	0.39455 (12)	0.5504 (5)	0.2719 (2)	0.0331 (6)
C8	0.28150 (12)	0.0637 (5)	0.1698 (2)	0.0410 (6)
H8	0.2739	0.0663	0.0929	0.049*
C9	0.24668 (12)	−0.1189 (6)	0.2024 (2)	0.0397 (6)
C10	0.19806 (13)	−0.2619 (5)	0.1154 (2)	0.0373 (6)
C11	0.16267 (13)	−0.4294 (5)	0.1442 (2)	0.0402 (6)
C12	0.17733 (14)	−0.4550 (6)	0.2600 (3)	0.0494 (7)
H12	0.1539	−0.5652	0.2800	0.059*
C13	0.22640 (17)	−0.3188 (7)	0.3461 (3)	0.0568 (8)
H13	0.2365	−0.3425	0.4239	0.068*
C14	0.26058 (14)	−0.1489 (6)	0.3189 (3)	0.0511 (7)
H14	0.2928	−0.0541	0.3777	0.061*
C15	0.13382 (18)	−0.0901 (7)	−0.0739 (3)	0.0626 (9)
H15A	0.0978	−0.1745	−0.0802	0.094*
H15B	0.1305	−0.0775	−0.1500	0.094*
H15C	0.1377	0.0850	−0.0418	0.094*
C16	0.07976 (15)	−0.7352 (7)	0.0833 (3)	0.0522 (8)
H16A	0.1058	−0.8754	0.1318	0.078*
H16B	0.0471	−0.8098	0.0130	0.078*
H16C	0.0628	−0.6404	0.1247	0.078*
H1A	0.3388 (18)	0.390 (8)	0.1239 (12)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0413 (13)	0.0432 (12)	0.0305 (11)	−0.0079 (10)	0.0183 (10)	0.0016 (10)
N2	0.0402 (13)	0.0420 (12)	0.0389 (12)	−0.0023 (10)	0.0218 (11)	0.0052 (10)
O1	0.0542 (12)	0.0502 (11)	0.0279 (9)	−0.0175 (9)	0.0200 (9)	−0.0075 (8)
O2	0.0498 (13)	0.0441 (10)	0.0430 (11)	−0.0080 (9)	0.0225 (10)	0.0053 (9)
O3	0.0624 (12)	0.0486 (11)	0.0298 (10)	−0.0120 (10)	0.0245 (9)	−0.0017 (8)
O4	0.0543 (11)	0.0553 (11)	0.0400 (10)	−0.0028 (10)	0.0287 (9)	−0.0038 (9)
O5	0.0572 (13)	0.0550 (12)	0.0458 (11)	−0.0207 (10)	0.0250 (10)	−0.0085 (10)
C1	0.0341 (14)	0.0323 (13)	0.0292 (13)	0.0034 (10)	0.0158 (11)	0.0007 (10)
C2	0.0334 (14)	0.0320 (12)	0.0283 (13)	−0.0011 (11)	0.0156 (12)	−0.0025 (10)
C3	0.0403 (14)	0.0374 (13)	0.0271 (12)	0.0005 (11)	0.0167 (11)	0.0003 (10)
C4	0.0369 (13)	0.0315 (13)	0.0364 (14)	−0.0001 (11)	0.0200 (12)	0.0023 (11)
C5	0.0414 (15)	0.0442 (15)	0.0329 (14)	−0.0100 (12)	0.0147 (12)	−0.0065 (11)
C6	0.0422 (14)	0.0434 (14)	0.0256 (12)	−0.0048 (12)	0.0140 (11)	−0.0029 (10)
C7	0.0386 (14)	0.0347 (13)	0.0289 (13)	0.0000 (11)	0.0188 (11)	−0.0017 (10)
C8	0.0422 (16)	0.0453 (15)	0.0337 (14)	−0.0037 (12)	0.0169 (12)	0.0042 (12)
C9	0.0393 (15)	0.0403 (14)	0.0405 (15)	−0.0003 (12)	0.0203 (12)	0.0036 (12)
C10	0.0409 (14)	0.0359 (14)	0.0384 (14)	0.0023 (11)	0.0219 (12)	−0.0012 (11)
C11	0.0421 (15)	0.0377 (14)	0.0445 (16)	−0.0027 (12)	0.0240 (13)	−0.0027 (12)
C12	0.0541 (18)	0.0520 (16)	0.0466 (17)	−0.0134 (14)	0.0281 (15)	0.0027 (14)
C13	0.0626 (19)	0.0684 (19)	0.0375 (16)	−0.0169 (17)	0.0228 (15)	0.0044 (15)
C14	0.0495 (17)	0.0559 (17)	0.0392 (16)	−0.0146 (14)	0.0146 (14)	0.0000 (13)
C15	0.073 (2)	0.070 (2)	0.0394 (17)	0.0109 (18)	0.0230 (16)	0.0041 (15)
C16	0.0493 (18)	0.0521 (17)	0.058 (2)	−0.0127 (14)	0.0284 (16)	−0.0027 (14)

N1—C7	1.342 (3)	C5—C6	1.371 (4)
N1—N2	1.382 (3)	C5—H5	0.9300
N1—H1A	0.893 (10)	C6—H6	0.9300
N2—C8	1.272 (3)	C8—C9	1.461 (4)
O1—C2	1.365 (3)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.394 (4)
O2—C4	1.354 (3)	C9—C14	1.397 (4)
O2—H2	0.8200	C10—C11	1.397 (3)
O3—C7	1.239 (3)	C11—C12	1.380 (4)
O4—C10	1.386 (3)	C12—C13	1.378 (4)
O4—C15	1.425 (4)	C12—H12	0.9300
O5—C11	1.364 (3)	C13—C14	1.369 (4)
O5—C16	1.430 (3)	C13—H13	0.9300
C1—C6	1.394 (3)	C14—H14	0.9300
C1—C2	1.406 (3)	C15—H15A	0.9600
C1—C7	1.489 (3)	C15—H15B	0.9600
C2—C3	1.384 (3)	C15—H15C	0.9600
C3—C4	1.387 (4)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.389 (4)	C16—H16C	0.9600
C7—N1—N2	119.8 (2)	C9—C8—H8	119.2
C7—N1—H1A	118 (3)	C10—C9—C14	119.5 (2)
N2—N1—H1A	122 (3)	C10—C9—C8	119.3 (2)
C8—N2—N1	115.2 (2)	C14—C9—C8	121.2 (3)
C2—O1—H1	109.5	O4—C10—C9	119.4 (2)
C4—O2—H2	109.5	O4—C10—C11	120.4 (2)
C10—O4—C15	114.5 (2)	C9—C10—C11	120.2 (2)
C11—O5—C16	116.9 (2)	O5—C11—C12	124.2 (2)
C6—C1—C2	116.6 (2)	O5—C11—C10	116.7 (2)
C6—C1—C7	117.5 (2)	C12—C11—C10	119.1 (2)
C2—C1—C7	125.9 (2)	C11—C12—C13	120.5 (3)
O1—C2—C3	118.9 (2)	C11—C12—H12	119.7
O1—C2—C1	119.8 (2)	C13—C12—H12	119.7
C3—C2—C1	121.2 (2)	C14—C13—C12	121.1 (3)
C4—C3—C2	120.2 (2)	C14—C13—H13	119.5
C4—C3—H3	119.9	C12—C13—H13	119.5
C2—C3—H3	119.9	C13—C14—C9	119.6 (3)
O2—C4—C3	122.0 (2)	C13—C14—H14	120.2
O2—C4—C5	118.4 (2)	C9—C14—H14	120.2
C3—C4—C5	119.6 (2)	O4—C15—H15A	109.5
C6—C5—C4	119.4 (2)	O4—C15—H15B	109.5
C6—C5—H5	120.3	H15A—C15—H15B	109.5
C4—C5—H5	120.3	O4—C15—H15C	109.5
C5—C6—C1	122.9 (2)	H15A—C15—H15C	109.5
C5—C6—H6	118.6	H15B—C15—H15C	109.5
C1—C6—H6	118.6	O5—C16—H16A	109.5
O3—C7—N1	120.7 (2)	O5—C16—H16B	109.5
O3—C7—C1	121.7 (2)	H16A—C16—H16B	109.5
N1—C7—C1	117.6 (2)	O5—C16—H16C	109.5
N2—C8—C9	121.6 (3)	H16A—C16—H16C	109.5
N2—C8—H8	119.2	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89 (1)	1.93 (3)	2.661 (3)	138 (4)
O1—H1···O3i	0.82	2.16	2.872 (3)	146
O2—H2···O3ii	0.82	1.90	2.706 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.89 (1)	1.93 (3)	2.661 (3)	138 (4)
O1—H1⋯O3i	0.82	2.16	2.872 (3)	146
O2—H2⋯O3ii	0.82	1.90	2.706 (3)	166

Symmetry codes: (i) ; (ii) .