N'-(2,4-Dimethoxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide ethanol solvate.

The title compound, C(16)H(16)N(2)O(6)·C(2)H(5)OH, was synthesized from 3,4,5-trihydroxy-benzoyl-hydrazide and 2,4-dimethoxy-benzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydr-oxy groups are involved in both intra-molecular O-H⋯O and inter-molecular O-H⋯N and O-H⋯O hydrogen bonds and a C-H⋯O interaction also occurs.

Related literature

For related compounds, see Abdul Alhadi et al. (2009 ▶). For the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see Lyubchova et al. (1995 ▶).

Experimental

Crystal data

C16H16N2O6·C2H6O

M = 378.38

Monoclinic,

a = 7.8347 (1) Å

b = 17.5412 (3) Å

c = 13.0230 (2) Å

β = 93.936 (1)°

V = 1785.53 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.31 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.987

19580 measured reflections

5188 independent reflections

3586 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.02

5188 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018947/hg2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018947/hg2510Isup2.hkl

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

C16H16N2O6·C2H6O	F(000) = 800
Mr = 378.38	Dx = 1.408 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3445 reflections
a = 7.8347 (1) Å	θ = 2.8–29.1°
b = 17.5412 (3) Å	µ = 0.11 mm−1
c = 13.0230 (2) Å	T = 100 K
β = 93.936 (1)°	Block, yellow
V = 1785.53 (5) Å3	0.31 × 0.16 × 0.12 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5188 independent reflections
Radiation source: fine-focus sealed tube	3586 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.967, Tmax = 0.987	k = −24→24
19580 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.3538P] where P = (Fo2 + 2Fc2)/3
5188 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.26 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
C1	1.15941 (17)	0.21466 (7)	0.76768 (10)	0.0156 (3)
H1	1.1458	0.2583	0.7248	0.019*
C2	1.25203 (17)	0.22016 (7)	0.86245 (10)	0.0153 (3)
C3	1.26837 (17)	0.15678 (8)	0.92716 (10)	0.0154 (3)
C4	1.19696 (18)	0.08744 (8)	0.89317 (10)	0.0170 (3)
C5	1.10756 (18)	0.08150 (8)	0.79830 (10)	0.0176 (3)
H5	1.0605	0.0339	0.7760	0.021*
C6	1.08672 (17)	0.14571 (7)	0.73529 (10)	0.0154 (3)
C7	0.98683 (17)	0.14395 (8)	0.63409 (10)	0.0159 (3)
C8	0.74521 (17)	0.00842 (8)	0.49550 (10)	0.0168 (3)
H8	0.7539	−0.0296	0.5476	0.023 (4)*
C9	0.64100 (17)	−0.00596 (8)	0.40063 (10)	0.0165 (3)
C10	0.57036 (17)	−0.07846 (8)	0.38154 (10)	0.0163 (3)
C11	0.47202 (17)	−0.09404 (8)	0.29061 (10)	0.0172 (3)
H11	0.4236	−0.1431	0.2785	0.021*
C12	0.44633 (18)	−0.03640 (8)	0.21828 (11)	0.0188 (3)
C13	0.51352 (19)	0.03637 (8)	0.23587 (11)	0.0209 (3)
H13	0.4939	0.0754	0.1859	0.025*
C14	0.60860 (18)	0.05093 (8)	0.32640 (11)	0.0190 (3)
H14	0.6533	0.1007	0.3389	0.023*
C15	0.2879 (2)	−0.11915 (8)	0.09897 (11)	0.0227 (3)
H15A	0.3824	−0.1557	0.0978	0.034*
H15B	0.2270	−0.1169	0.0307	0.034*
H15C	0.2087	−0.1354	0.1498	0.034*
C16	0.5321 (2)	−0.20516 (8)	0.44383 (12)	0.0247 (3)
H16A	0.4072	−0.2007	0.4358	0.037*
H16B	0.5647	−0.2364	0.5044	0.037*
H16C	0.5737	−0.2292	0.3824	0.037*
C17	0.7901 (2)	0.81507 (9)	0.72385 (14)	0.0313 (4)
H19A	0.6929	0.8370	0.6826	0.047*
H19B	0.7482	0.7866	0.7818	0.047*
H19C	0.8531	0.7806	0.6809	0.047*
C18	0.9073 (2)	0.87827 (9)	0.76416 (12)	0.0259 (3)
H18A	0.8458	0.9110	0.8113	0.031*
H18B	1.0074	0.8559	0.8038	0.031*
N1	0.92094 (15)	0.07647 (6)	0.60343 (9)	0.0168 (2)
H1'	0.9379	0.0357	0.6422	0.030 (5)*
N2	0.82556 (15)	0.07168 (6)	0.50974 (9)	0.0174 (2)
O1	0.96209 (13)	0.20261 (5)	0.58110 (7)	0.0219 (2)
O2	1.32670 (14)	0.28879 (5)	0.88620 (7)	0.0218 (2)
H2	1.3569	0.2901	0.9493	0.033*
O3	1.35316 (13)	0.15568 (6)	1.02261 (7)	0.0209 (2)
H3	1.3877	0.1998	1.0381	0.031*
O4	1.21299 (15)	0.02350 (6)	0.95174 (8)	0.0273 (3)
H4	1.2718	0.0332	1.0065	0.041*
O5	0.60584 (13)	−0.13118 (6)	0.45673 (7)	0.0224 (2)
O6	0.35424 (14)	−0.04532 (6)	0.12604 (8)	0.0264 (3)
O7	0.96498 (14)	0.92367 (6)	0.68270 (8)	0.0229 (2)
H7	1.0291	0.8975	0.6475	0.034*

	U11	U22	U33	U12	U13	U23
C1	0.0190 (6)	0.0138 (6)	0.0137 (6)	0.0025 (5)	−0.0015 (5)	0.0010 (5)
C2	0.0187 (6)	0.0123 (6)	0.0148 (6)	−0.0006 (5)	0.0000 (5)	−0.0015 (5)
C3	0.0175 (6)	0.0163 (6)	0.0119 (6)	0.0006 (5)	−0.0021 (5)	−0.0010 (5)
C4	0.0214 (7)	0.0143 (6)	0.0147 (6)	0.0000 (5)	−0.0029 (5)	0.0027 (5)
C5	0.0223 (7)	0.0140 (6)	0.0159 (7)	−0.0007 (5)	−0.0034 (5)	−0.0003 (5)
C6	0.0171 (6)	0.0156 (6)	0.0131 (6)	0.0011 (5)	−0.0020 (5)	−0.0006 (5)
C7	0.0175 (6)	0.0157 (6)	0.0141 (6)	0.0019 (5)	−0.0016 (5)	−0.0005 (5)
C8	0.0194 (7)	0.0158 (6)	0.0148 (6)	0.0008 (5)	−0.0021 (5)	0.0007 (5)
C9	0.0170 (6)	0.0168 (6)	0.0151 (7)	−0.0002 (5)	−0.0021 (5)	−0.0009 (5)
C10	0.0187 (7)	0.0162 (6)	0.0139 (6)	0.0010 (5)	−0.0010 (5)	0.0013 (5)
C11	0.0188 (7)	0.0162 (6)	0.0161 (6)	−0.0014 (5)	−0.0020 (5)	−0.0015 (5)
C12	0.0201 (7)	0.0192 (7)	0.0162 (7)	0.0000 (5)	−0.0059 (5)	−0.0012 (5)
C13	0.0274 (8)	0.0156 (6)	0.0186 (7)	−0.0001 (6)	−0.0065 (6)	0.0026 (5)
C14	0.0208 (7)	0.0141 (6)	0.0212 (7)	−0.0009 (5)	−0.0040 (5)	−0.0008 (5)
C15	0.0287 (8)	0.0186 (7)	0.0197 (7)	−0.0034 (6)	−0.0074 (6)	−0.0025 (6)
C16	0.0339 (8)	0.0158 (7)	0.0236 (8)	−0.0045 (6)	−0.0042 (6)	0.0033 (6)
C17	0.0369 (9)	0.0197 (7)	0.0381 (10)	−0.0044 (7)	0.0079 (7)	−0.0009 (7)
C18	0.0344 (8)	0.0217 (7)	0.0212 (7)	0.0002 (6)	−0.0020 (6)	0.0049 (6)
N1	0.0215 (6)	0.0151 (5)	0.0129 (5)	−0.0010 (4)	−0.0063 (4)	0.0013 (4)
N2	0.0199 (6)	0.0172 (6)	0.0142 (6)	0.0000 (5)	−0.0064 (4)	−0.0011 (4)
O1	0.0323 (6)	0.0142 (5)	0.0176 (5)	0.0012 (4)	−0.0101 (4)	0.0016 (4)
O2	0.0353 (6)	0.0145 (5)	0.0145 (5)	−0.0057 (4)	−0.0070 (4)	0.0012 (4)
O3	0.0310 (6)	0.0167 (5)	0.0137 (5)	−0.0028 (4)	−0.0079 (4)	0.0011 (4)
O4	0.0446 (7)	0.0167 (5)	0.0184 (5)	−0.0065 (5)	−0.0141 (5)	0.0056 (4)
O5	0.0320 (6)	0.0162 (5)	0.0177 (5)	−0.0042 (4)	−0.0076 (4)	0.0030 (4)
O6	0.0382 (6)	0.0176 (5)	0.0209 (5)	−0.0043 (4)	−0.0160 (5)	0.0010 (4)
O7	0.0295 (6)	0.0163 (5)	0.0232 (6)	0.0001 (4)	0.0034 (4)	−0.0001 (4)

C1—C6	1.3900 (18)	C13—C14	1.3745 (19)
C1—C2	1.3914 (18)	C13—H13	0.9500
C1—H1	0.9500	C14—H14	0.9500
C2—O2	1.3647 (15)	C15—O6	1.4308 (16)
C2—C3	1.3958 (18)	C15—H15A	0.9800
C3—O3	1.3687 (15)	C15—H15B	0.9800
C3—C4	1.3979 (18)	C15—H15C	0.9800
C4—O4	1.3574 (16)	C16—O5	1.4258 (17)
C4—C5	1.3818 (18)	C16—H16A	0.9800
C5—C6	1.3965 (18)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.4862 (18)	C17—C18	1.511 (2)
C7—O1	1.2466 (16)	C17—H19A	0.9800
C7—N1	1.3412 (17)	C17—H19B	0.9800
C8—N2	1.2830 (17)	C17—H19C	0.9800
C8—C9	1.4554 (18)	C18—O7	1.4247 (18)
C8—H8	0.9500	C18—H18A	0.9900
C9—C14	1.4004 (19)	C18—H18B	0.9900
C9—C10	1.4023 (18)	N1—N2	1.3889 (15)
C10—O5	1.3615 (16)	N1—H1'	0.8800
C10—C11	1.3948 (18)	O2—H2	0.8400
C11—C12	1.3869 (19)	O3—H3	0.8400
C11—H11	0.9500	O4—H4	0.8400
C12—O6	1.3672 (16)	O7—H7	0.8400
C12—C13	1.3938 (19)
C6—C1—C2	120.50 (12)	C12—C13—H13	120.4
C6—C1—H1	119.8	C13—C14—C9	121.44 (13)
C2—C1—H1	119.8	C13—C14—H14	119.3
O2—C2—C1	116.85 (12)	C9—C14—H14	119.3
O2—C2—C3	123.07 (11)	O6—C15—H15A	109.5
C1—C2—C3	120.06 (12)	O6—C15—H15B	109.5
O3—C3—C2	125.32 (12)	H15A—C15—H15B	109.5
O3—C3—C4	115.73 (11)	O6—C15—H15C	109.5
C2—C3—C4	118.93 (11)	H15A—C15—H15C	109.5
O4—C4—C5	117.51 (12)	H15B—C15—H15C	109.5
O4—C4—C3	121.43 (12)	O5—C16—H16A	109.5
C5—C4—C3	121.07 (12)	O5—C16—H16B	109.5
C4—C5—C6	119.75 (12)	H16A—C16—H16B	109.5
C4—C5—H5	120.1	O5—C16—H16C	109.5
C6—C5—H5	120.1	H16A—C16—H16C	109.5
C1—C6—C5	119.63 (12)	H16B—C16—H16C	109.5
C1—C6—C7	117.84 (11)	C18—C17—H19A	109.5
C5—C6—C7	122.52 (12)	C18—C17—H19B	109.5
O1—C7—N1	121.44 (12)	H19A—C17—H19B	109.5
O1—C7—C6	121.75 (12)	C18—C17—H19C	109.5
N1—C7—C6	116.79 (12)	H19A—C17—H19C	109.5
N2—C8—C9	120.91 (12)	H19B—C17—H19C	109.5
N2—C8—H8	119.5	O7—C18—C17	111.58 (13)
C9—C8—H8	119.5	O7—C18—H18A	109.3
C14—C9—C10	118.24 (12)	C17—C18—H18A	109.3
C14—C9—C8	121.81 (12)	O7—C18—H18B	109.3
C10—C9—C8	119.95 (12)	C17—C18—H18B	109.3
O5—C10—C11	123.45 (12)	H18A—C18—H18B	108.0
O5—C10—C9	115.45 (11)	C7—N1—N2	119.19 (11)
C11—C10—C9	121.09 (12)	C7—N1—H1'	120.4
C12—C11—C10	118.67 (12)	N2—N1—H1'	120.4
C12—C11—H11	120.7	C8—N2—N1	114.10 (11)
C10—C11—H11	120.7	C2—O2—H2	109.5
O6—C12—C11	123.82 (12)	C3—O3—H3	109.5
O6—C12—C13	114.82 (12)	C4—O4—H4	109.5
C11—C12—C13	121.36 (12)	C10—O5—C16	118.18 (11)
C14—C13—C12	119.17 (13)	C12—O6—C15	118.75 (11)
C14—C13—H13	120.4	C18—O7—H7	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	2.54	2.9325 (13)	109
O3—H3···O2	0.84	2.54	2.9325 (13)	110
O4—H4···O3	0.84	2.25	2.7009 (14)	114
N1—H1'···O7i	0.88	2.04	2.8844 (15)	160
O2—H2···O1ii	0.84	1.86	2.6871 (13)	170
O2—H2···N2ii	0.84	2.57	2.9293 (15)	107
O3—H3···O1ii	0.84	1.88	2.7200 (13)	177
O4—H4···O6iii	0.84	2.14	2.7366 (14)	127
C14—H14···O2iv	0.95	2.42	3.3539 (17)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84	2.54	2.9325 (13)	109
O3—H3⋯O2	0.84	2.54	2.9325 (13)	110
O4—H4⋯O3	0.84	2.25	2.7009 (14)	114
N1—H1′⋯O7i	0.88	2.04	2.8844 (15)	160
O2—H2⋯O1ii	0.84	1.86	2.6871 (13)	170
O2—H2⋯N2ii	0.84	2.57	2.9293 (15)	107
O3—H3⋯O1ii	0.84	1.88	2.7200 (13)	177
O4—H4⋯O6iii	0.84	2.14	2.7366 (14)	127
C14—H14⋯O2iv	0.95	2.42	3.3539 (17)	167

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