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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1026.
Published online 2010 April 2. doi:  10.1107/S1600536810012122
PMCID: PMC2979136

N′-(2,3-Dimethoxy­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

Abstract

In the title compound, C17H18N2O4, the dihedral angle between the two benzene rings is 6.0 (2)° and the mol­ecule adopts an E configuration with respect to the C=N bond. There is an intra­molecular O—H(...)O hydrogen bond in the mol­ecule, which generates an S(6) ring. In the crystal, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For a related structure and background information, see: Han & Zhao (2010 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1026-scheme1.jpg

Experimental

Crystal data

  • C17H18N2O4
  • M r = 314.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1026-efi1.jpg
  • a = 14.923 (3) Å
  • b = 24.329 (5) Å
  • c = 8.7422 (17) Å
  • V = 3174.0 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.17 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.984, T max = 0.986
  • 17128 measured reflections
  • 3461 independent reflections
  • 1998 reflections with I > 2σ(I)
  • R int = 0.223

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.175
  • S = 0.92
  • 3461 reflections
  • 211 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.30 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012122/hb5386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012122/hb5386Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

As part of our ongoing studies of hydrazones (Han & Zhao, 2010), we now report the structure of the title compound, (I).

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 6.0 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O–H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Experimental

A mixture of 2,3-dimethoxybenzaldehyde (0.166 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 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

H atoms were positioned geometrically and refined using the riding-model approximation, with C–H = 0.93 or 0.96 Å, O–H = 0.82 Å, N–H = 0.90 Å, and Uiso(H) = 1.2Ueq(C,N) or Uiso(H) = 1.5Ueq(methyl C and O).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids for non-H atoms. Intramolecular O–H···O hydrogen bond is shown as a dashed line.
Fig. 2.
The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C17H18N2O4F(000) = 1328
Mr = 314.33Dx = 1.316 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 2994 reflections
a = 14.923 (3) Åθ = 2.7–24.9°
b = 24.329 (5) ŵ = 0.10 mm1
c = 8.7422 (17) ÅT = 298 K
V = 3174.0 (11) Å3Block, colorless
Z = 80.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer3461 independent reflections
Radiation source: fine-focus sealed tube1998 reflections with I > 2σ(I)
graphiteRint = 0.223
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −18→18
Tmin = 0.984, Tmax = 0.986k = −30→31
17128 measured reflectionsl = −8→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3
3461 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

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)

xyzUiso*/Ueq
O10.42606 (9)0.10101 (6)0.37153 (16)0.0482 (4)
O20.28300 (9)0.06224 (8)0.52262 (16)0.0602 (5)
O30.84543 (10)0.11847 (7)0.62612 (16)0.0586 (5)
O41.01095 (9)0.13449 (7)0.53290 (16)0.0601 (5)
H40.97160.12320.59030.072*
N10.67827 (11)0.09279 (7)0.53655 (18)0.0464 (5)
N20.74005 (11)0.11742 (7)0.44045 (19)0.0474 (5)
H2A0.72740.12350.34110.057*
C10.52468 (13)0.06866 (8)0.5673 (2)0.0402 (5)
C20.43791 (13)0.07538 (9)0.5098 (2)0.0396 (5)
C30.36482 (13)0.05310 (9)0.5889 (2)0.0443 (5)
C40.37887 (16)0.02333 (10)0.7208 (2)0.0521 (6)
H4A0.33060.00790.77270.063*
C50.46507 (16)0.01651 (10)0.7758 (2)0.0536 (6)
H50.4743−0.00360.86490.064*
C60.53705 (15)0.03885 (9)0.7014 (2)0.0473 (5)
H60.59450.03410.74060.057*
C70.38589 (19)0.15360 (11)0.3766 (3)0.0724 (8)
H7A0.33360.15230.44050.109*
H7B0.36900.16460.27510.109*
H7C0.42780.17970.41780.109*
C80.20603 (16)0.04196 (12)0.6008 (3)0.0701 (8)
H8A0.20710.00250.60090.105*
H8B0.15290.05460.55000.105*
H8C0.20630.05510.70430.105*
C90.59903 (13)0.09237 (9)0.4826 (2)0.0445 (5)
H90.58850.10760.38670.053*
C100.82117 (13)0.13106 (9)0.4951 (2)0.0428 (5)
C110.88015 (14)0.16270 (8)0.3910 (2)0.0421 (5)
C120.97309 (14)0.16251 (8)0.4165 (2)0.0456 (5)
C131.03102 (15)0.19180 (10)0.3209 (3)0.0532 (6)
C140.99399 (18)0.22279 (10)0.2061 (3)0.0650 (7)
H141.03180.24300.14290.078*
C150.90212 (19)0.22521 (11)0.1802 (3)0.0671 (7)
H150.87890.24690.10210.081*
C160.84659 (15)0.19497 (9)0.2724 (2)0.0538 (6)
H160.78510.19600.25540.065*
C171.13038 (15)0.18931 (13)0.3465 (3)0.0768 (8)
H17A1.15020.15190.33920.115*
H17B1.14420.20340.44640.115*
H17C1.16030.21110.27050.115*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0396 (8)0.0589 (10)0.0462 (9)0.0034 (7)−0.0010 (6)0.0099 (7)
O20.0318 (8)0.0918 (13)0.0569 (10)−0.0080 (8)0.0014 (7)0.0109 (8)
O30.0378 (8)0.0921 (13)0.0459 (9)−0.0056 (8)−0.0042 (7)0.0152 (8)
O40.0370 (9)0.0835 (12)0.0597 (10)0.0003 (8)−0.0035 (7)0.0124 (8)
N10.0348 (10)0.0580 (12)0.0463 (10)−0.0030 (8)−0.0004 (8)0.0027 (8)
N20.0375 (10)0.0623 (12)0.0422 (10)−0.0061 (9)−0.0030 (8)0.0055 (8)
C10.0371 (11)0.0444 (12)0.0390 (11)−0.0017 (9)−0.0027 (9)−0.0038 (9)
C20.0373 (11)0.0444 (11)0.0372 (11)−0.0011 (9)−0.0012 (9)0.0006 (9)
C30.0377 (12)0.0543 (13)0.0409 (11)−0.0030 (10)0.0018 (9)−0.0034 (10)
C40.0520 (14)0.0595 (15)0.0448 (12)−0.0075 (11)0.0059 (11)0.0020 (10)
C50.0616 (15)0.0590 (14)0.0403 (12)0.0016 (12)−0.0011 (11)0.0102 (10)
C60.0470 (13)0.0505 (13)0.0445 (12)0.0015 (10)−0.0070 (10)0.0015 (10)
C70.0754 (19)0.0632 (18)0.0787 (17)0.0105 (14)−0.0018 (15)0.0187 (14)
C80.0411 (14)0.102 (2)0.0677 (16)−0.0099 (13)0.0149 (11)−0.0004 (14)
C90.0368 (12)0.0531 (13)0.0436 (12)0.0003 (9)−0.0030 (9)0.0007 (10)
C100.0348 (11)0.0501 (12)0.0437 (12)0.0008 (10)−0.0017 (9)−0.0012 (9)
C110.0410 (12)0.0432 (12)0.0422 (11)−0.0039 (9)−0.0031 (9)−0.0042 (9)
C120.0440 (13)0.0456 (12)0.0472 (12)−0.0001 (10)−0.0006 (10)−0.0079 (10)
C130.0461 (13)0.0532 (14)0.0602 (14)−0.0050 (11)0.0092 (11)−0.0077 (11)
C140.0723 (18)0.0547 (15)0.0680 (16)−0.0191 (13)0.0149 (14)0.0024 (12)
C150.0768 (19)0.0569 (16)0.0678 (16)−0.0098 (13)−0.0064 (14)0.0206 (12)
C160.0519 (13)0.0512 (14)0.0584 (14)−0.0029 (11)−0.0090 (11)0.0061 (11)
C170.0450 (15)0.087 (2)0.098 (2)−0.0091 (14)0.0176 (14)−0.0022 (16)

Geometric parameters (Å, °)

O1—C21.372 (2)C7—H7A0.9600
O1—C71.414 (3)C7—H7B0.9600
O2—C31.370 (2)C7—H7C0.9600
O2—C81.425 (3)C8—H8A0.9600
O3—C101.240 (2)C8—H8B0.9600
O4—C121.349 (2)C8—H8C0.9600
O4—H40.8195C9—H90.9300
N1—C91.273 (3)C10—C111.482 (3)
N1—N21.384 (2)C11—C161.394 (3)
N2—C101.343 (2)C11—C121.405 (3)
N2—H2A0.9005C12—C131.398 (3)
C1—C61.391 (3)C13—C141.372 (3)
C1—C21.398 (3)C13—C171.501 (3)
C1—C91.453 (3)C14—C151.391 (4)
C2—C31.401 (3)C14—H140.9300
C3—C41.378 (3)C15—C161.370 (3)
C4—C51.383 (3)C15—H150.9300
C4—H4A0.9300C16—H160.9300
C5—C61.368 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C2—O1—C7115.99 (16)O2—C8—H8C109.5
C3—O2—C8117.34 (18)H8A—C8—H8C109.5
C12—O4—H4109.3H8B—C8—H8C109.5
C9—N1—N2113.41 (17)N1—C9—C1121.57 (19)
C10—N2—N1119.45 (17)N1—C9—H9119.2
C10—N2—H2A119.4C1—C9—H9119.2
N1—N2—H2A121.1O3—C10—N2122.05 (19)
C6—C1—C2119.12 (18)O3—C10—C11121.49 (18)
C6—C1—C9122.34 (18)N2—C10—C11116.46 (17)
C2—C1—C9118.53 (18)C16—C11—C12118.3 (2)
O1—C2—C1119.28 (17)C16—C11—C10122.42 (19)
O1—C2—C3120.71 (17)C12—C11—C10119.17 (18)
C1—C2—C3119.90 (18)O4—C12—C13116.7 (2)
O2—C3—C4125.12 (18)O4—C12—C11122.34 (19)
O2—C3—C2114.99 (18)C13—C12—C11120.9 (2)
C4—C3—C2119.87 (19)C14—C13—C12117.9 (2)
C3—C4—C5119.7 (2)C14—C13—C17122.0 (2)
C3—C4—H4A120.2C12—C13—C17120.1 (2)
C5—C4—H4A120.2C13—C14—C15122.6 (2)
C6—C5—C4121.1 (2)C13—C14—H14118.7
C6—C5—H5119.4C15—C14—H14118.7
C4—C5—H5119.4C16—C15—C14118.6 (2)
C5—C6—C1120.25 (19)C16—C15—H15120.7
C5—C6—H6119.9C14—C15—H15120.7
C1—C6—H6119.9C15—C16—C11121.5 (2)
O1—C7—H7A109.5C15—C16—H16119.2
O1—C7—H7B109.5C11—C16—H16119.2
H7A—C7—H7B109.5C13—C17—H17A109.5
O1—C7—H7C109.5C13—C17—H17B109.5
H7A—C7—H7C109.5H17A—C17—H17B109.5
H7B—C7—H7C109.5C13—C17—H17C109.5
O2—C8—H8A109.5H17A—C17—H17C109.5
O2—C8—H8B109.5H17B—C17—H17C109.5
H8A—C8—H8B109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···O30.821.912.630 (2)146
N2—H2A···O3i0.902.173.030 (2)158

Symmetry codes: (i) −x+3/2, y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5386).

References

  • 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.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1025. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography