(2,4-Dimethoxy-benzyl-idene)-2-hydroxy-benzohydrazide ethanol solvate.

In the planar title mol-ecule, C(16)H(16)N(2)O(4)·C(2)H(6)O, the planar Schiff base molecule is linked to the ethanol solvent mol-ecule by a hydr-oxy-amide hydrogen bond. The hydr-oxy group of the ethanol mol-ecule is a hydrogen-bond donor to the double-bonded N atom of an adjacent Sciff base, pairs of interactions taking place across a center of symmetry and giving rise to a hydrogen-bonded dimer.

Related literature

For the crystal structures of other substituted benzyl­idene-2-hydroxy­benzohydrazides, see: Li (2007 ▶); Liang et al. (2005 ▶); Luo (2007 ▶); Ma et al. (2005 ▶); Pan & Yang (2005a ▶,b ▶,c ▶); Qiu et al. (2006 ▶); Shao et al. (2004 ▶); Wang et al. (2007 ▶); Xu & Liu (2006 ▶); Yang (2006 ▶); Yang & Pan (2004 ▶, 2005a ▶,b ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

pan class="CellLine">C16H16N2O4·pan class="Chemical">C2H6O

M = 346.38

Monoclinic,

a = 7.7909 (2) Å

b = 18.0539 (6) Å

c = 12.0001 (4) Å

β = 93.803 (2)°

V = 1684.17 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 (2) K

0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART pan class="Gene">APEX diffractometer

Absorption correction: none

13796 measured reflections

3853 independent reflections

2575 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.03

3853 reflections

241 parameters

3 restraints

pan class="Disease">H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: pan class="Gene">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 global, I. DOI: 10.1107/S1600536808011768/sg2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011768/sg2239Isup2.hkl

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

C16H16N2O4·C2H6O	F000 = 736
Mr = 346.38	Dx = 1.366 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1895 reflections
a = 7.7909 (2) Å	θ = 2.8–25.5º
b = 18.0539 (6) Å	µ = 0.10 mm−1
c = 12.0001 (4) Å	T = 100 (2) K
β = 93.803 (2)º	Prism, colorless
V = 1684.17 (9) Å3	0.20 × 0.15 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	2575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.0º
ω scans	h = −10→10
Absorption correction: None	k = −20→23
13796 measured reflections	l = −15→15
3853 independent reflections

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.175P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3853 reflections	Δρmax = 0.21 e Å−3
241 parameters	Δρmin = −0.24 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.64682 (15)	0.22307 (7)	0.69448 (11)	0.0248 (3)
O2	0.48542 (15)	0.30514 (7)	0.55256 (10)	0.0253 (3)
O3	0.09164 (14)	0.62457 (7)	0.44328 (10)	0.0224 (3)
O4	−0.15888 (16)	0.55131 (7)	0.07909 (10)	0.0280 (3)
O5	0.45339 (16)	0.56902 (7)	0.68732 (11)	0.0256 (3)
N1	0.40917 (17)	0.42200 (9)	0.59366 (12)	0.0191 (3)
N2	0.32044 (17)	0.42928 (8)	0.48948 (11)	0.0195 (3)
C1	0.6546 (2)	0.28297 (10)	0.76338 (14)	0.0199 (4)
C2	0.7381 (2)	0.27412 (10)	0.86870 (14)	0.0219 (4)
H2	0.7858	0.2275	0.8904	0.026*
C3	0.7514 (2)	0.33316 (11)	0.94120 (14)	0.0231 (4)
H3	0.8073	0.3266	1.0133	0.028*
C4	0.6847 (2)	0.40220 (10)	0.91101 (14)	0.0230 (4)
H4	0.6962	0.4428	0.9614	0.028*
C5	0.6014 (2)	0.41094 (10)	0.80671 (14)	0.0211 (4)
H5	0.5560	0.4581	0.7856	0.025*
C6	0.5825 (2)	0.35172 (10)	0.73132 (14)	0.0180 (4)
C7	0.4908 (2)	0.35796 (10)	0.61929 (14)	0.0192 (4)
C8	0.22902 (19)	0.48872 (10)	0.47864 (14)	0.0188 (4)
H8	0.2277	0.5226	0.5391	0.023*
C9	0.1282 (2)	0.50446 (10)	0.37526 (14)	0.0185 (4)
C10	0.0552 (2)	0.57510 (10)	0.35888 (14)	0.0189 (4)
C11	−0.0433 (2)	0.59274 (10)	0.26156 (14)	0.0197 (4)
H11	−0.0930	0.6405	0.2519	0.024*
C12	−0.0677 (2)	0.53942 (10)	0.17899 (14)	0.0213 (4)
C13	0.0016 (2)	0.46857 (10)	0.19353 (15)	0.0227 (4)
H13	−0.0173	0.4321	0.1369	0.027*
C14	0.0973 (2)	0.45200 (10)	0.29057 (14)	0.0205 (4)
H14	0.1438	0.4036	0.3004	0.025*
C15	0.0125 (2)	0.69592 (10)	0.43449 (15)	0.0240 (4)
H15A	0.0456	0.7250	0.5015	0.036*
H15B	−0.1128	0.6902	0.4275	0.036*
H15C	0.0505	0.7215	0.3685	0.036*
C16	−0.2167 (2)	0.62483 (11)	0.05390 (16)	0.0281 (4)
H16A	−0.2707	0.6264	−0.0222	0.042*
H16B	−0.1184	0.6588	0.0597	0.042*
H16C	−0.3006	0.6398	0.1069	0.042*
C17	0.4115 (2)	0.62589 (11)	0.76362 (15)	0.0278 (4)
H17A	0.5186	0.6506	0.7929	0.033*
H17B	0.3567	0.6033	0.8275	0.033*
C18	0.2921 (2)	0.68255 (11)	0.70951 (16)	0.0310 (5)
H18A	0.2608	0.7187	0.7655	0.046*
H18B	0.1881	0.6579	0.6775	0.046*
H18C	0.3496	0.7079	0.6502	0.046*
H1O	0.594 (3)	0.2375 (13)	0.6331 (12)	0.054 (7)*
H5O	0.518 (2)	0.5858 (13)	0.6389 (15)	0.052 (7)*
H1N	0.410 (3)	0.4596 (8)	0.6371 (14)	0.036 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0311 (7)	0.0185 (7)	0.0241 (7)	0.0015 (5)	−0.0021 (6)	−0.0001 (6)
O2	0.0328 (7)	0.0185 (7)	0.0236 (7)	0.0024 (5)	−0.0045 (5)	−0.0035 (6)
O3	0.0291 (6)	0.0170 (7)	0.0208 (7)	0.0034 (5)	−0.0009 (5)	−0.0022 (5)
O4	0.0342 (7)	0.0261 (8)	0.0225 (7)	0.0032 (6)	−0.0077 (5)	0.0004 (6)
O5	0.0313 (7)	0.0212 (7)	0.0247 (7)	0.0003 (6)	0.0063 (6)	−0.0036 (6)
N1	0.0227 (7)	0.0181 (8)	0.0163 (8)	−0.0002 (6)	−0.0007 (6)	−0.0006 (7)
N2	0.0206 (7)	0.0205 (8)	0.0169 (8)	−0.0006 (6)	−0.0012 (6)	0.0010 (7)
C1	0.0190 (8)	0.0193 (10)	0.0218 (9)	−0.0023 (7)	0.0033 (7)	−0.0003 (8)
C2	0.0212 (8)	0.0210 (10)	0.0233 (10)	0.0009 (7)	0.0000 (7)	0.0044 (8)
C3	0.0224 (8)	0.0285 (11)	0.0183 (9)	−0.0043 (8)	0.0001 (7)	0.0050 (8)
C4	0.0263 (9)	0.0235 (10)	0.0194 (9)	−0.0042 (7)	0.0031 (7)	−0.0034 (8)
C5	0.0221 (8)	0.0181 (10)	0.0232 (10)	−0.0003 (7)	0.0022 (7)	0.0017 (8)
C6	0.0192 (8)	0.0169 (10)	0.0181 (9)	−0.0020 (7)	0.0018 (6)	0.0009 (7)
C7	0.0187 (8)	0.0176 (10)	0.0214 (9)	−0.0012 (7)	0.0024 (7)	−0.0001 (8)
C8	0.0190 (8)	0.0181 (9)	0.0198 (9)	−0.0010 (7)	0.0044 (7)	0.0001 (8)
C9	0.0191 (8)	0.0187 (9)	0.0179 (9)	−0.0014 (7)	0.0032 (6)	0.0005 (8)
C10	0.0181 (8)	0.0193 (10)	0.0196 (9)	−0.0026 (7)	0.0043 (7)	−0.0026 (8)
C11	0.0195 (8)	0.0179 (10)	0.0218 (9)	0.0012 (7)	0.0027 (7)	0.0028 (8)
C12	0.0210 (8)	0.0228 (10)	0.0200 (9)	−0.0026 (7)	0.0009 (7)	0.0018 (8)
C13	0.0253 (9)	0.0206 (10)	0.0218 (10)	−0.0024 (7)	−0.0006 (7)	−0.0034 (8)
C14	0.0217 (8)	0.0158 (9)	0.0240 (10)	−0.0014 (7)	0.0023 (7)	0.0007 (8)
C15	0.0268 (9)	0.0187 (10)	0.0267 (10)	0.0036 (7)	0.0032 (7)	−0.0032 (8)
C16	0.0288 (9)	0.0294 (11)	0.0254 (10)	0.0027 (8)	−0.0031 (8)	0.0047 (9)
C17	0.0319 (10)	0.0270 (11)	0.0245 (10)	0.0004 (8)	0.0026 (8)	−0.0066 (9)
C18	0.0323 (10)	0.0270 (12)	0.0339 (11)	0.0002 (8)	0.0040 (8)	−0.0023 (9)

O1—C1	1.360 (2)	C8—C9	1.452 (2)
O1—H1O	0.859 (9)	C8—H8	0.9500
O2—C7	1.244 (2)	C9—C14	1.398 (2)
O3—C10	1.366 (2)	C9—C10	1.405 (2)
O3—C15	1.429 (2)	C10—C11	1.391 (2)
O4—C12	1.369 (2)	C11—C12	1.385 (2)
O4—C16	1.428 (2)	C11—H11	0.9500
O5—C17	1.428 (2)	C12—C13	1.395 (2)
O5—H5O	0.848 (10)	C13—C14	1.374 (2)
N1—C7	1.345 (2)	C13—H13	0.9500
N1—N2	1.3941 (19)	C14—H14	0.9500
N1—H1N	0.855 (9)	C15—H15A	0.9800
N2—C8	1.290 (2)	C15—H15B	0.9800
C1—C2	1.392 (2)	C15—H15C	0.9800
C1—C6	1.405 (2)	C16—H16A	0.9800
C2—C3	1.375 (2)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.389 (3)	C17—C18	1.501 (3)
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.380 (2)	C17—H17B	0.9900
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.402 (2)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.485 (2)
C1—O1—H1O	106.2 (16)	C11—C10—C9	121.39 (16)
C10—O3—C15	117.86 (13)	C12—C11—C10	118.89 (16)
C12—O4—C16	117.97 (14)	C12—C11—H11	120.6
C17—O5—H5O	110.7 (17)	C10—C11—H11	120.6
C7—N1—N2	119.00 (15)	O4—C12—C11	123.77 (16)
C7—N1—H1N	123.9 (14)	O4—C12—C13	115.29 (16)
N2—N1—H1N	117.1 (14)	C11—C12—C13	120.94 (16)
C8—N2—N1	113.99 (14)	C14—C13—C12	119.31 (17)
O1—C1—C2	117.39 (16)	C14—C13—H13	120.3
O1—C1—C6	122.35 (15)	C12—C13—H13	120.3
C2—C1—C6	120.27 (16)	C13—C14—C9	121.74 (17)
C3—C2—C1	119.77 (17)	C13—C14—H14	119.1
C3—C2—H2	120.1	C9—C14—H14	119.1
C1—C2—H2	120.1	O3—C15—H15A	109.5
C2—C3—C4	121.28 (16)	O3—C15—H15B	109.5
C2—C3—H3	119.4	H15A—C15—H15B	109.5
C4—C3—H3	119.4	O3—C15—H15C	109.5
C5—C4—C3	118.97 (17)	H15A—C15—H15C	109.5
C5—C4—H4	120.5	H15B—C15—H15C	109.5
C3—C4—H4	120.5	O4—C16—H16A	109.5
C4—C5—C6	121.40 (17)	O4—C16—H16B	109.5
C4—C5—H5	119.3	H16A—C16—H16B	109.5
C6—C5—H5	119.3	O4—C16—H16C	109.5
C5—C6—C1	118.29 (15)	H16A—C16—H16C	109.5
C5—C6—C7	123.38 (16)	H16B—C16—H16C	109.5
C1—C6—C7	118.32 (15)	O5—C17—C18	111.97 (15)
O2—C7—N1	121.10 (16)	O5—C17—H17A	109.2
O2—C7—C6	121.22 (15)	C18—C17—H17A	109.2
N1—C7—C6	117.66 (15)	O5—C17—H17B	109.2
N2—C8—C9	120.86 (16)	C18—C17—H17B	109.2
N2—C8—H8	119.6	H17A—C17—H17B	107.9
C9—C8—H8	119.6	C17—C18—H18A	109.5
C14—C9—C10	117.70 (15)	C17—C18—H18B	109.5
C14—C9—C8	123.06 (16)	H18A—C18—H18B	109.5
C10—C9—C8	119.23 (16)	C17—C18—H18C	109.5
O3—C10—C11	123.27 (16)	H18A—C18—H18C	109.5
O3—C10—C9	115.32 (15)	H18B—C18—H18C	109.5
C7—N1—N2—C8	171.60 (15)	N2—C8—C9—C14	12.2 (2)
O1—C1—C2—C3	179.24 (15)	N2—C8—C9—C10	−168.70 (15)
C6—C1—C2—C3	−0.6 (2)	C15—O3—C10—C11	5.3 (2)
C1—C2—C3—C4	−0.8 (2)	C15—O3—C10—C9	−176.25 (14)
C2—C3—C4—C5	1.0 (2)	C14—C9—C10—O3	−178.97 (14)
C3—C4—C5—C6	0.2 (2)	C8—C9—C10—O3	1.9 (2)
C4—C5—C6—C1	−1.6 (2)	C14—C9—C10—C11	−0.5 (2)
C4—C5—C6—C7	178.61 (15)	C8—C9—C10—C11	−179.61 (15)
O1—C1—C6—C5	−178.08 (14)	O3—C10—C11—C12	177.63 (14)
C2—C1—C6—C5	1.7 (2)	C9—C10—C11—C12	−0.7 (2)
O1—C1—C6—C7	1.8 (2)	C16—O4—C12—C11	6.8 (2)
C2—C1—C6—C7	−178.44 (14)	C16—O4—C12—C13	−173.16 (15)
N2—N1—C7—O2	−1.3 (2)	C10—C11—C12—O4	−178.49 (15)
N2—N1—C7—C6	−179.38 (13)	C10—C11—C12—C13	1.5 (2)
C5—C6—C7—O2	175.88 (16)	O4—C12—C13—C14	179.01 (14)
C1—C6—C7—O2	−4.0 (2)	C11—C12—C13—C14	−0.9 (3)
C5—C6—C7—N1	−6.1 (2)	C12—C13—C14—C9	−0.3 (3)
C1—C6—C7—N1	174.10 (15)	C10—C9—C14—C13	1.0 (2)
N1—N2—C8—C9	−179.75 (14)	C8—C9—C14—C13	−179.89 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.86 (1)	1.74 (2)	2.528 (2)	151 (2)
O5—H5o···N2i	0.85 (1)	2.07 (1)	2.847 (2)	152 (2)
N1—H1n···O5	0.86 (1)	2.09 (1)	2.894 (2)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2	0.86 (1)	1.74 (2)	2.528 (2)	151 (2)
O5—H5o⋯N2i	0.85 (1)	2.07 (1)	2.847 (2)	152 (2)
N1—H1n⋯O5	0.86 (1)	2.09 (1)	2.894 (2)	157 (2)

Symmetry code: (i) .