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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1027
https://doi.org/10.1107/S1600536810012134

N′-(2,3-Di­meth­oxy­benzyl­­idene)-2,4-di­hydroxy­benzohydrazide

You-Yue Hana* and Qiu-Rong Zhaoa

aDepartment of Chemistry and Life Science, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
*Correspondence e-mail: hanyouyue@126.com

(Received 30 March 2010; accepted 30 March 2010; online 10 April 2010)

In the title compound, C16H16N2O5, the dihedral angle between the two benzene rings is 8.5 (3)° and the mol­ecule adopts an E configuration with respect to the C=N bond. There is an intra­molecular N—H⋯O hydrogen bond in the mol­ecule, which generates an S(6) ring. In the crystal, mol­ecules are linked through inter­molecular O—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related structures and background information, see: Han & Zhao (2010a[Han, Y.-Y. & Zhao, Q.-R. (2010a). Acta Cryst. E66, o1025.],b[Han, Y.-Y. & Zhao, Q.-R. (2010b). Acta Cryst. E66, o1026.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C16H16N2O5

  • Mr = 316.31

  • Monoclinic, C c

  • 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.980

  • 3934 measured reflections

  • 1549 independent reflections

  • 1247 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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

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) [x, -y+1, z-{\script{1\over 2}}]; (ii) [x, -y+2, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012134/hb5385sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012134/hb5385Isup2.hkl

checkCIF report


Comment top

As part of our ongoing structural studies of hydrazone compounds (Han & Zhao, 2010a,b), we now report the sturcture of the title compound, (I).

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 8.5 (3)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular N–H···O hydrogen bond (Table 1) in the molecule.

In the crystal structure, molecules are linked through intermolecular O–H···O hydrogen bonds (Table 1) to form layers parallel to the bc plane (Fig. 2).

Related literature top

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

Experimental top

A mixture of 2,3-dimethoxybenzaldehyde (0.166 g, 1 mmol) and 2,4-dihydroxybenzohydrazide (0.168 g, 1 mmol) in 50 ml me thanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, colourless blocks of (I) were formed.

Refinement top

H1A was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The other H atoms were positioned geometrically and refined using the riding-model approximation, with C–H = 0.93 or 0.96 Å, and O–H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(methyl C and O). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Structure description top

As part of our ongoing structural studies of hydrazone compounds (Han & Zhao, 2010a,b), we now report the sturcture of the title compound, (I).

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 8.5 (3)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular N–H···O hydrogen bond (Table 1) in the molecule.

In the crystal structure, molecules are linked through intermolecular O–H···O hydrogen bonds (Table 1) to form layers parallel to the bc plane (Fig. 2).

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

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids for non-H atoms. Intramolecular N–H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The molecular packing of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines.
N'-(2,3-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide top
Crystal data top
C16H16N2O5F(000) = 664
Mr = 316.31Dx = 1.466 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1397 reflections
a = 24.918 (4) Åθ = 2.7–25.0°
b = 5.0291 (8) ŵ = 0.11 mm−1
c = 13.075 (2) ÅT = 298 K
β = 118.994 (2)°Block, colourless
V = 1433.1 (4) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		1549 independent reflections
Radiation source: fine-focus sealed tube1247 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −23→31
Tmin = 0.978, Tmax = 0.980k = −6→6
3934 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H 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 parametersΔρmax = 0.15 e Å−3
3 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C16H16N2O5V = 1433.1 (4) Å3
Mr = 316.31Z = 4
Monoclinic, CcMo Kα radiation
a = 24.918 (4) ŵ = 0.11 mm−1
b = 5.0291 (8) ÅT = 298 K
c = 13.075 (2) Å0.20 × 0.20 × 0.18 mm
β = 118.994 (2)°
Data collection top
Bruker SMART CCD
diffractometer		1549 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1247 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.980Rint = 0.047
3934 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0343 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 0.78Δρmax = 0.15 e Å−3
1549 reflectionsΔρmin = −0.15 e Å−3
215 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.34984 (10)0.3854 (5)0.19993 (19)0.0380 (5)
N20.32187 (10)0.2191 (4)0.24411 (19)0.0393 (5)
O10.35804 (9)0.5925 (4)0.02075 (15)0.0441 (5)
H10.36040.5886−0.03960.066*
O20.49643 (9)1.3145 (4)0.09920 (16)0.0456 (5)
H20.47451.33950.02890.068*
O30.41233 (10)0.5503 (4)0.37839 (17)0.0460 (5)
O40.18657 (10)−0.2434 (4)0.00073 (18)0.0474 (5)
O50.11485 (10)−0.5565 (4)0.05383 (18)0.0526 (6)
C10.42086 (11)0.7354 (5)0.2189 (2)0.0317 (5)
C20.40165 (11)0.7604 (5)0.0990 (2)0.0310 (5)
C30.42595 (12)0.9539 (5)0.0580 (2)0.0348 (5)
H30.41170.9707−0.02190.042*
C40.47143 (12)1.1230 (5)0.1358 (2)0.0339 (6)
C50.49350 (13)1.0928 (5)0.2551 (2)0.0409 (6)
H50.52541.19950.30820.049*
C60.46786 (12)0.9044 (5)0.2941 (2)0.0381 (6)
H60.48250.88860.37410.046*
C70.39455 (12)0.5504 (5)0.2719 (2)0.0331 (6)
C80.28150 (12)0.0637 (5)0.1698 (2)0.0410 (6)
H80.27390.06630.09290.049*
C90.24668 (12)−0.1189 (6)0.2024 (2)0.0397 (6)
C100.19806 (13)−0.2619 (5)0.1154 (2)0.0373 (6)
C110.16267 (13)−0.4294 (5)0.1442 (2)0.0402 (6)
C120.17733 (14)−0.4550 (6)0.2600 (3)0.0494 (7)
H120.1539−0.56520.28000.059*
C130.22640 (17)−0.3188 (7)0.3461 (3)0.0568 (8)
H130.2365−0.34250.42390.068*
C140.26058 (14)−0.1489 (6)0.3189 (3)0.0511 (7)
H140.2928−0.05410.37770.061*
C150.13382 (18)−0.0901 (7)−0.0739 (3)0.0626 (9)
H15A0.0978−0.1745−0.08020.094*
H15B0.1305−0.0775−0.15000.094*
H15C0.13770.0850−0.04180.094*
C160.07976 (15)−0.7352 (7)0.0833 (3)0.0522 (8)
H16A0.1058−0.87540.13180.078*
H16B0.0471−0.80980.01300.078*
H16C0.0628−0.64040.12470.078*
H1A0.3388 (18)0.390 (8)0.1239 (12)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0413 (13)0.0432 (12)0.0305 (11)−0.0079 (10)0.0183 (10)0.0016 (10)
N20.0402 (13)0.0420 (12)0.0389 (12)−0.0023 (10)0.0218 (11)0.0052 (10)
O10.0542 (12)0.0502 (11)0.0279 (9)−0.0175 (9)0.0200 (9)−0.0075 (8)
O20.0498 (13)0.0441 (10)0.0430 (11)−0.0080 (9)0.0225 (10)0.0053 (9)
O30.0624 (12)0.0486 (11)0.0298 (10)−0.0120 (10)0.0245 (9)−0.0017 (8)
O40.0543 (11)0.0553 (11)0.0400 (10)−0.0028 (10)0.0287 (9)−0.0038 (9)
O50.0572 (13)0.0550 (12)0.0458 (11)−0.0207 (10)0.0250 (10)−0.0085 (10)
C10.0341 (14)0.0323 (13)0.0292 (13)0.0034 (10)0.0158 (11)0.0007 (10)
C20.0334 (14)0.0320 (12)0.0283 (13)−0.0011 (11)0.0156 (12)−0.0025 (10)
C30.0403 (14)0.0374 (13)0.0271 (12)0.0005 (11)0.0167 (11)0.0003 (10)
C40.0369 (13)0.0315 (13)0.0364 (14)−0.0001 (11)0.0200 (12)0.0023 (11)
C50.0414 (15)0.0442 (15)0.0329 (14)−0.0100 (12)0.0147 (12)−0.0065 (11)
C60.0422 (14)0.0434 (14)0.0256 (12)−0.0048 (12)0.0140 (11)−0.0029 (10)
C70.0386 (14)0.0347 (13)0.0289 (13)0.0000 (11)0.0188 (11)−0.0017 (10)
C80.0422 (16)0.0453 (15)0.0337 (14)−0.0037 (12)0.0169 (12)0.0042 (12)
C90.0393 (15)0.0403 (14)0.0405 (15)−0.0003 (12)0.0203 (12)0.0036 (12)
C100.0409 (14)0.0359 (14)0.0384 (14)0.0023 (11)0.0219 (12)−0.0012 (11)
C110.0421 (15)0.0377 (14)0.0445 (16)−0.0027 (12)0.0240 (13)−0.0027 (12)
C120.0541 (18)0.0520 (16)0.0466 (17)−0.0134 (14)0.0281 (15)0.0027 (14)
C130.0626 (19)0.0684 (19)0.0375 (16)−0.0169 (17)0.0228 (15)0.0044 (15)
C140.0495 (17)0.0559 (17)0.0392 (16)−0.0146 (14)0.0146 (14)0.0000 (13)
C150.073 (2)0.070 (2)0.0394 (17)0.0109 (18)0.0230 (16)0.0041 (15)
C160.0493 (18)0.0521 (17)0.058 (2)−0.0127 (14)0.0284 (16)−0.0027 (14)
Geometric parameters (Å, º) top
N1—C71.342 (3)C5—C61.371 (4)
N1—N21.382 (3)C5—H50.9300
N1—H1A0.893 (10)C6—H60.9300
N2—C81.272 (3)C8—C91.461 (4)
O1—C21.365 (3)C8—H80.9300
O1—H10.8200C9—C101.394 (4)
O2—C41.354 (3)C9—C141.397 (4)
O2—H20.8200C10—C111.397 (3)
O3—C71.239 (3)C11—C121.380 (4)
O4—C101.386 (3)C12—C131.378 (4)
O4—C151.425 (4)C12—H120.9300
O5—C111.364 (3)C13—C141.369 (4)
O5—C161.430 (3)C13—H130.9300
C1—C61.394 (3)C14—H140.9300
C1—C21.406 (3)C15—H15A0.9600
C1—C71.489 (3)C15—H15B0.9600
C2—C31.384 (3)C15—H15C0.9600
C3—C41.387 (4)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.389 (4)C16—H16C0.9600
C7—N1—N2119.8 (2)C9—C8—H8119.2
C7—N1—H1A118 (3)C10—C9—C14119.5 (2)
N2—N1—H1A122 (3)C10—C9—C8119.3 (2)
C8—N2—N1115.2 (2)C14—C9—C8121.2 (3)
C2—O1—H1109.5O4—C10—C9119.4 (2)
C4—O2—H2109.5O4—C10—C11120.4 (2)
C10—O4—C15114.5 (2)C9—C10—C11120.2 (2)
C11—O5—C16116.9 (2)O5—C11—C12124.2 (2)
C6—C1—C2116.6 (2)O5—C11—C10116.7 (2)
C6—C1—C7117.5 (2)C12—C11—C10119.1 (2)
C2—C1—C7125.9 (2)C11—C12—C13120.5 (3)
O1—C2—C3118.9 (2)C11—C12—H12119.7
O1—C2—C1119.8 (2)C13—C12—H12119.7
C3—C2—C1121.2 (2)C14—C13—C12121.1 (3)
C4—C3—C2120.2 (2)C14—C13—H13119.5
C4—C3—H3119.9C12—C13—H13119.5
C2—C3—H3119.9C13—C14—C9119.6 (3)
O2—C4—C3122.0 (2)C13—C14—H14120.2
O2—C4—C5118.4 (2)C9—C14—H14120.2
C3—C4—C5119.6 (2)O4—C15—H15A109.5
C6—C5—C4119.4 (2)O4—C15—H15B109.5
C6—C5—H5120.3H15A—C15—H15B109.5
C4—C5—H5120.3O4—C15—H15C109.5
C5—C6—C1122.9 (2)H15A—C15—H15C109.5
C5—C6—H6118.6H15B—C15—H15C109.5
C1—C6—H6118.6O5—C16—H16A109.5
O3—C7—N1120.7 (2)O5—C16—H16B109.5
O3—C7—C1121.7 (2)H16A—C16—H16B109.5
N1—C7—C1117.6 (2)O5—C16—H16C109.5
N2—C8—C9121.6 (3)H16A—C16—H16C109.5
N2—C8—H8119.2H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.89 (1)1.93 (3)2.661 (3)138 (4)
O1—H1···O3i0.822.162.872 (3)146
O2—H2···O3ii0.821.902.706 (3)166
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formulaC16H16N2O5
Mr316.31
Crystal system, space groupMonoclinic, Cc
Temperature (K)298
a, b, c (Å)24.918 (4), 5.0291 (8), 13.075 (2)
β (°) 118.994 (2)
V (Å3)1433.1 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.978, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		3934, 1549, 1247
Rint0.047
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.089, 0.78
No. of reflections1549
No. of parameters215
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.15

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.893 (10)1.93 (3)2.661 (3)138 (4)
O1—H1···O3i0.822.162.872 (3)146
O2—H2···O3ii0.821.902.706 (3)166
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2.
 

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (No. 200802187 C). The authors thank Mr Yuan-Guang Zhang of Anqing Normal University for his help with growing the crystals.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHan, Y.-Y. & Zhao, Q.-R. (2010a). Acta Cryst. E66, o1025.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHan, Y.-Y. & Zhao, Q.-R. (2010b). Acta Cryst. E66, o1026.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1027
https://doi.org/10.1107/S1600536810012134
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