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Journal List > Acta Crystallogr Sect E Struct Rep Online > v.64(Pt 9); Sep 1, 2008

Formats:
Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1824.
Published online 2008 August 23. doi: 10.1107/S1600536808026846.
PMCID: PMC2960481
Copyright © Yehye et al. 2008
N-Acetyl-2-hydroxy-N′-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide
Wagee A. Yehye,a Noorsaadah Abdul Rahman,a Azhar Ariffin,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 19, 2008; Accepted August 20, 2008.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Abstract
In the crystal structure of the title Schiff-base, C20H21N3O4, the amino group forms an N—H[cdots, three dots, centered]O hydrogen bond to the acetyl group of an adjacent mol­ecule, forming a zigzag chain. The 2-hydr­oxy group is inter­nally hydrogen bonded to the amido group though an O—H[cdots, three dots, centered]O hydrogen bond.
Related literature
For medicinal uses of the precursor Schiff base, see: Jin et al. (2006 [triangle]); Joshi et al. (2008 [triangle]); Szczepankiewicz et al. (2001 [triangle]).
Click on image to enlarge
An external file that holds a picture, illustration, etc. Object name is e-64-o1824-scheme1.jpg Object name is e-64-o1824-scheme1.jpg
Crystal data
  • C20H21N3O4
  • M r = 367.40
  • Monoclinic, An external file that holds a picture, illustration, etc. Object name is e-64-o1824-efi1.jpg
  • a = 11.0075 (3) Å
  • b = 10.5197 (3) Å
  • c = 15.4479 (4) Å
  • β = 93.967 (2)°
  • V = 1784.51 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 (2) K
  • 0.20 × 0.15 × 0.10 mm
Data collection
  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 16316 measured reflections
  • 4072 independent reflections
  • 2646 reflections with I > 2σ(I)
  • R int = 0.065
Refinement
  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.120
  • S = 1.02
  • 4072 reflections
  • 255 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.26 e Å−3
Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026846/tk2298sup1.cif
Click here to view.(20K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026846/tk2298Isup2.hkl
Click here to view.(200K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the University of Malaya for supporting this study (grant No. FS338/2008 A).
supplementary crystallographic information
Comment
The Schiff base, N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide, exhibits useful medicinal properties (Jin et al., 2006; Joshi et al., 2008; Szczepankiewicz et al., 2001). When dissolved in acetic anhydride, the compound undergoes a reaction to yield the title compound, (I), Fig. 1. Essentially, a mole of methyl acetate has been added across the carbon-nitrogen double-bond. In the crystal structure of (I), the amino group forms an N–H···O hydrogen bond to the acetyl group of an adjacent molecule to result in a zigzag chain that runs along the b-axis of the orthorhombic unit cell, Table 1. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O–H···O hydrogen bond, Table 1.
Experimental
2-Hydroxybenzohydrazide was condensed with 1-methylindole-3-carboxaldehyde to yield the corresponding Schiff base. To N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide (0.88 g, 3 mmol) was added acetic anhydride (10 ml). The mixture was heated to 398–403 K until the reactants dissolved completely. After 2 h of heating, the mixture was cooled and then treated with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated and the resulting solid was recrystallized from methanol to give (I) as colorless crystals.
Refinement
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The hydroxy- and ammonium H-atoms were located in a difference Fourier map, and were refined with a distance restraints O–H = N–H = 0.85±0.01 Å; their temperature factors were freely refined.
Figures
Fig. 1.
Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of (I) drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
C20H21N3O4F000 = 776
Mr = 367.40Dx = 1.367 Mg m−3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1739 reflections
a = 11.0075 (3) Åθ = 2.2–21.4º
b = 10.5197 (3) ŵ = 0.10 mm−1
c = 15.4479 (4) ÅT = 100 (2) K
β = 93.967 (2)ºBlock, colorless
V = 1784.51 (8) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection
Bruker SMART APEX diffractometer2646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.2º
ω scansh = −14→14
Absorption correction: Nonek = −13→13
16316 measured reflectionsl = −20→20
4072 independent reflections
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120  w = 1/[σ2(Fo2) + (0.0466P)2 + 0.3679P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4072 reflectionsΔρmax = 0.26 e Å−3
255 parametersΔρmin = −0.26 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
O10.75833 (13)0.62701 (15)0.28349 (10)0.0328 (4)
H1O0.717 (2)0.5560 (16)0.2811 (18)0.069 (10)*
O20.57533 (11)0.47150 (13)0.28757 (9)0.0266 (3)
O30.27682 (12)0.25872 (13)0.22300 (9)0.0279 (3)
O40.41144 (11)0.35118 (13)0.43051 (8)0.0257 (3)
N10.38731 (14)0.55433 (15)0.29735 (10)0.0197 (4)
H1N0.3430 (17)0.6189 (15)0.3061 (14)0.037 (6)*
N20.33109 (13)0.43653 (14)0.29605 (10)0.0188 (3)
N30.12618 (13)0.52539 (15)0.40494 (10)0.0205 (4)
C10.68446 (17)0.7144 (2)0.31706 (12)0.0262 (5)
C20.73287 (19)0.8337 (2)0.33795 (14)0.0315 (5)
H20.81440.85300.32620.038*
C30.6634 (2)0.9230 (2)0.37533 (14)0.0354 (5)
H30.69721.00420.38920.042*
C40.54370 (19)0.8971 (2)0.39356 (13)0.0308 (5)
H40.49660.95920.42090.037*
C50.49478 (18)0.78036 (18)0.37132 (12)0.0249 (4)
H50.41320.76210.38370.030*
C60.56213 (17)0.68846 (18)0.33118 (12)0.0225 (4)
C70.51091 (17)0.56257 (18)0.30497 (11)0.0207 (4)
C80.31298 (16)0.36884 (19)0.22067 (12)0.0221 (4)
C90.33655 (19)0.4356 (2)0.13833 (13)0.0294 (5)
H9A0.30080.38670.08890.044*
H9B0.42460.44350.13370.044*
H9C0.29970.52040.13830.044*
C100.30451 (16)0.38509 (18)0.38166 (12)0.0212 (4)
H100.25040.30910.37360.025*
C110.24263 (16)0.48432 (18)0.43178 (12)0.0208 (4)
C120.28551 (17)0.55066 (18)0.50327 (12)0.0227 (4)
H120.36240.54000.53430.027*
C130.19310 (17)0.63891 (18)0.52267 (12)0.0222 (4)
C140.18300 (18)0.73351 (19)0.58605 (12)0.0261 (5)
H140.24740.74770.62910.031*
C150.07752 (18)0.8057 (2)0.58468 (13)0.0282 (5)
H150.07040.87080.62670.034*
C16−0.01854 (18)0.7841 (2)0.52232 (13)0.0295 (5)
H16−0.08990.83480.52300.035*
C17−0.01235 (17)0.6909 (2)0.45972 (13)0.0260 (5)
H17−0.07850.67540.41820.031*
C180.09490 (16)0.62076 (18)0.46006 (12)0.0220 (4)
C190.05096 (17)0.4838 (2)0.32897 (12)0.0269 (5)
H19A−0.03510.48720.34150.040*
H19B0.07260.39630.31440.040*
H19C0.06470.53970.27990.040*
C200.4677 (2)0.24041 (19)0.39780 (14)0.0313 (5)
H20A0.53950.21830.43580.047*
H20B0.49240.25740.33920.047*
H20C0.40970.16960.39600.047*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
O10.0245 (7)0.0335 (9)0.0408 (9)−0.0008 (7)0.0048 (6)0.0009 (7)
O20.0224 (7)0.0240 (8)0.0339 (8)0.0036 (6)0.0054 (6)−0.0027 (6)
O30.0311 (8)0.0184 (8)0.0342 (8)−0.0058 (6)0.0016 (6)−0.0067 (6)
O40.0282 (7)0.0211 (8)0.0272 (7)0.0051 (6)−0.0028 (6)−0.0001 (6)
N10.0201 (8)0.0107 (8)0.0284 (9)−0.0007 (7)0.0024 (7)−0.0012 (7)
N20.0219 (8)0.0112 (8)0.0235 (8)−0.0031 (6)0.0023 (6)−0.0011 (7)
N30.0213 (8)0.0190 (9)0.0213 (8)−0.0025 (7)0.0010 (6)−0.0028 (7)
C10.0270 (10)0.0277 (12)0.0236 (10)−0.0010 (9)−0.0011 (8)0.0057 (9)
C20.0291 (11)0.0302 (12)0.0345 (12)−0.0109 (10)−0.0027 (9)0.0081 (10)
C30.0452 (13)0.0230 (12)0.0364 (12)−0.0101 (10)−0.0088 (10)0.0048 (10)
C40.0420 (13)0.0197 (11)0.0297 (11)−0.0021 (9)−0.0028 (10)−0.0017 (9)
C50.0296 (10)0.0209 (11)0.0239 (10)−0.0027 (9)−0.0014 (8)0.0013 (9)
C60.0252 (10)0.0184 (10)0.0236 (10)−0.0025 (8)0.0000 (8)0.0049 (8)
C70.0243 (10)0.0205 (10)0.0172 (9)−0.0013 (8)0.0020 (7)0.0030 (8)
C80.0194 (9)0.0207 (11)0.0259 (10)0.0033 (8)0.0002 (8)−0.0026 (8)
C90.0338 (11)0.0306 (12)0.0241 (10)−0.0007 (10)0.0028 (9)−0.0032 (9)
C100.0228 (9)0.0176 (10)0.0232 (10)−0.0010 (8)0.0007 (8)0.0005 (8)
C110.0222 (9)0.0175 (10)0.0228 (9)−0.0016 (8)0.0022 (8)0.0017 (8)
C120.0238 (10)0.0231 (11)0.0213 (9)0.0003 (8)0.0008 (8)0.0007 (8)
C130.0251 (10)0.0199 (10)0.0218 (10)−0.0024 (8)0.0036 (8)0.0030 (8)
C140.0304 (11)0.0268 (12)0.0216 (10)−0.0033 (9)0.0043 (8)−0.0024 (9)
C150.0356 (11)0.0238 (11)0.0263 (10)0.0006 (9)0.0090 (9)−0.0047 (9)
C160.0282 (11)0.0289 (12)0.0326 (11)0.0042 (9)0.0101 (9)0.0009 (10)
C170.0229 (10)0.0266 (11)0.0286 (11)−0.0011 (8)0.0036 (8)0.0012 (9)
C180.0236 (9)0.0193 (10)0.0236 (10)−0.0040 (8)0.0059 (8)0.0000 (8)
C190.0247 (10)0.0279 (12)0.0274 (11)−0.0023 (9)−0.0028 (8)−0.0050 (9)
C200.0367 (12)0.0185 (11)0.0378 (12)0.0085 (9)−0.0026 (10)0.0007 (9)
Geometric parameters (Å, °)
O1—C11.354 (2)C8—C91.491 (3)
O1—H1O0.871 (10)C9—H9A0.9800
O2—C71.233 (2)C9—H9B0.9800
O3—C81.226 (2)C9—H9C0.9800
O4—C101.400 (2)C10—C111.492 (3)
O4—C201.428 (2)C10—H101.0000
N1—C71.360 (2)C11—C121.363 (3)
N1—N21.385 (2)C12—C131.424 (3)
N1—H1N0.852 (9)C12—H120.9500
N2—C81.368 (2)C13—C141.406 (3)
N2—C101.477 (2)C13—C181.413 (3)
N3—C181.375 (2)C14—C151.387 (3)
N3—C111.389 (2)C14—H140.9500
N3—C191.456 (2)C15—C161.399 (3)
C1—C21.393 (3)C15—H150.9500
C1—C61.406 (3)C16—C171.382 (3)
C2—C31.365 (3)C16—H160.9500
C2—H20.9500C17—C181.392 (3)
C3—C41.393 (3)C17—H170.9500
C3—H30.9500C19—H19A0.9800
C4—C51.375 (3)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.390 (3)C20—H20A0.9800
C5—H50.9500C20—H20B0.9800
C6—C71.485 (3)C20—H20C0.9800
C1—O1—H1O106.0 (19)O4—C10—C11107.19 (14)
C10—O4—C20112.71 (14)N2—C10—C11109.52 (15)
C7—N1—N2120.11 (16)O4—C10—H10109.6
C7—N1—H1N121.0 (15)N2—C10—H10109.6
N2—N1—H1N117.1 (15)C11—C10—H10109.6
C8—N2—N1121.13 (15)C12—C11—N3110.09 (17)
C8—N2—C10123.05 (15)C12—C11—C10129.33 (17)
N1—N2—C10115.52 (14)N3—C11—C10120.52 (16)
C18—N3—C11107.92 (15)C11—C12—C13106.97 (16)
C18—N3—C19124.45 (16)C11—C12—H12126.5
C11—N3—C19127.50 (16)C13—C12—H12126.5
O1—C1—C2118.06 (18)C14—C13—C18118.61 (18)
O1—C1—C6122.32 (18)C14—C13—C12134.43 (18)
C2—C1—C6119.6 (2)C18—C13—C12106.95 (17)
C3—C2—C1120.1 (2)C15—C14—C13118.93 (18)
C3—C2—H2119.9C15—C14—H14120.5
C1—C2—H2119.9C13—C14—H14120.5
C2—C3—C4121.1 (2)C14—C15—C16120.91 (19)
C2—C3—H3119.4C14—C15—H15119.5
C4—C3—H3119.4C16—C15—H15119.5
C5—C4—C3118.9 (2)C17—C16—C15121.71 (19)
C5—C4—H4120.5C17—C16—H16119.1
C3—C4—H4120.5C15—C16—H16119.1
C4—C5—C6121.40 (19)C16—C17—C18117.16 (18)
C4—C5—H5119.3C16—C17—H17121.4
C6—C5—H5119.3C18—C17—H17121.4
C5—C6—C1118.71 (18)N3—C18—C17129.29 (17)
C5—C6—C7122.54 (17)N3—C18—C13108.07 (16)
C1—C6—C7118.73 (18)C17—C18—C13122.64 (18)
O2—C7—N1121.25 (17)N3—C19—H19A109.5
O2—C7—C6122.64 (17)N3—C19—H19B109.5
N1—C7—C6116.05 (17)H19A—C19—H19B109.5
O3—C8—N2119.69 (18)N3—C19—H19C109.5
O3—C8—C9123.09 (18)H19A—C19—H19C109.5
N2—C8—C9117.21 (17)H19B—C19—H19C109.5
C8—C9—H9A109.5O4—C20—H20A109.5
C8—C9—H9B109.5O4—C20—H20B109.5
H9A—C9—H9B109.5H20A—C20—H20B109.5
C8—C9—H9C109.5O4—C20—H20C109.5
H9A—C9—H9C109.5H20A—C20—H20C109.5
H9B—C9—H9C109.5H20B—C20—H20C109.5
O4—C10—N2111.40 (15)
C7—N1—N2—C8−84.8 (2)N1—N2—C10—C1148.99 (19)
C7—N1—N2—C1089.2 (2)C18—N3—C11—C120.6 (2)
O1—C1—C2—C3−177.23 (18)C19—N3—C11—C12176.65 (18)
C6—C1—C2—C32.8 (3)C18—N3—C11—C10−176.91 (16)
C1—C2—C3—C40.2 (3)C19—N3—C11—C10−0.9 (3)
C2—C3—C4—C5−1.6 (3)O4—C10—C11—C1211.2 (3)
C3—C4—C5—C6−0.1 (3)N2—C10—C11—C12−109.8 (2)
C4—C5—C6—C13.0 (3)O4—C10—C11—N3−171.84 (16)
C4—C5—C6—C7−178.81 (18)N2—C10—C11—N367.2 (2)
O1—C1—C6—C5175.68 (17)N3—C11—C12—C13−0.6 (2)
C2—C1—C6—C5−4.3 (3)C10—C11—C12—C13176.68 (18)
O1—C1—C6—C7−2.6 (3)C11—C12—C13—C14−178.7 (2)
C2—C1—C6—C7177.42 (17)C11—C12—C13—C180.3 (2)
N2—N1—C7—O219.8 (3)C18—C13—C14—C15−0.2 (3)
N2—N1—C7—C6−162.92 (15)C12—C13—C14—C15178.6 (2)
C5—C6—C7—O2−163.41 (18)C13—C14—C15—C161.0 (3)
C1—C6—C7—O214.8 (3)C14—C15—C16—C17−0.2 (3)
C5—C6—C7—N119.4 (3)C15—C16—C17—C18−1.3 (3)
C1—C6—C7—N1−162.41 (17)C11—N3—C18—C17−179.76 (19)
N1—N2—C8—O3171.07 (16)C19—N3—C18—C174.0 (3)
C10—N2—C8—O3−2.5 (3)C11—N3—C18—C13−0.4 (2)
N1—N2—C8—C9−10.1 (2)C19—N3—C18—C13−176.59 (17)
C10—N2—C8—C9176.32 (16)C16—C17—C18—N3−178.60 (19)
C20—O4—C10—N2−71.2 (2)C16—C17—C18—C132.1 (3)
C20—O4—C10—C11168.97 (15)C14—C13—C18—N3179.21 (16)
C8—N2—C10—O4104.46 (19)C12—C13—C18—N30.1 (2)
N1—N2—C10—O4−69.42 (19)C14—C13—C18—C17−1.4 (3)
C8—N2—C10—C11−137.13 (17)C12—C13—C18—C17179.47 (18)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
O1—H1o···O20.87 (1)1.81 (2)2.599 (2)150 (3)
N1—H1n···O3i0.85 (1)2.01 (1)2.812 (2)157 (2)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2.
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2298).
References
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  • Westrip, S. P. (2008). publCIF In preparation.
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