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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2473.
Published online 2009 September 16. doi:  10.1107/S1600536809036526
PMCID: PMC2970484

3-Methoxy­benzohydrazide

Abstract

The title compound, C8H10N2O2, crystallizes with two independent mol­ecules in an asymmetric unit. The structure is stabilized by nine inter­molecular N—H(...)N, N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008 [triangle], 2009a [triangle],b [triangle]); Jamal et al. (2008 [triangle], 2009 [triangle]); Kallel et al. (1992 [triangle]); Saraogi et al. (2002 [triangle]). For the biological activity of hydrazides, see: Ara et al. (2007 [triangle]); Ashiq, Ara et al. (2008 [triangle]).

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Object name is e-65-o2473-scheme1.jpg

Experimental

Crystal data

  • C8H10N2O2
  • M r = 166.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2473-efi1.jpg
  • a = 13.1288 (8) Å
  • b = 7.5417 (4) Å
  • c = 17.0734 (10) Å
  • β = 92.857 (3)°
  • V = 1688.40 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.39 × 0.15 × 0.11 mm

Data collection

  • Bruker KAPPA APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.979, T max = 0.990
  • 18386 measured reflections
  • 4200 independent reflections
  • 1708 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.126
  • S = 0.95
  • 4200 reflections
  • 237 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.22 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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809036526/pv2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036526/pv2207Isup2.hkl

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

Acknowledgments

The authors thank the Higher Education Commission, Pakistan, for providing the diffractometer at GCU, Lahore, and Bana International for their support in collecting the crystallographic data.

supplementary crystallographic information

Comment

Hydrazides constitute an important class of biologically active organic compounds (Ashiq, Ara et al., 2008; Ara et al., 2007). In searching for biologically active compounds we have synthesized the title compound, (I), and report its crystal structure in this paper.

The asymmetric unit of the title compound contains two crystallographically unique molecules (Fig. 1). The bond distances and bond angles in (I) are similar to the corresponding distances and angles reported in the structures of benzhydrazide (Kallel et al., 1992), para-chloro (Saraogi et al., 2002), para-bromo (Ashiq, Jamal et al., 2008),para-iodo (Jamal et al., 2008), para-methoxy (Ashiq, Jamal et al., 2009a), para-hydroxy (Jamal et al., 2009) and para-phenylsemicarbazide (Ashiq, Jamal et al., 2009b) analogues of (I).

In the crystal structure the molecules are held together by intermolecular hydrogen bonds of the types N—H···N, N—H···O and C—H···O (Table 1 and Fig. 2).

The title compound was found to be active against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging and inactive against α-glucosidase enzyme (Ashiq, Ara et al., 2008).

Experimental

All reagent-grade chemicals were obtained from Aldrich and Sigma Chemical companies and were used without further purification. To a solution of ethyl-3-methoxybenzoate (3.6 g, 20 mmol) in 75 ml ethanol, hydrazine hydrate (5.0 ml, 100 mmol) was added. The mixture was refluxed for 5 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford (I) (yield 79%). Crystal of the title compound suitable for X-ray crystallographic study were grown from a solution of methanol by slow evaporation at room temperature.

Refinement

The hydrogen atoms bonded to N atoms were taken from fourier synthesis and their coordinates were allowed to refine. The H atoms bonded to aryl and methyl C-atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å, respectively. The Uiso(H) were 1.2 times Ueq of aryl C and N atoms and 1.5 times Ueq of methyl C atoms.

Figures

Fig. 1.
ORTEP diagram of the title compound with the ellipsoids drawn at the 50% probability level, showing the atomic labels.
Fig. 2.
A unit cell packing diagram of (I) showing hydrogen bonds drawn by dashed lines. Hydrogen atoms not involved in H-bonding have been omitted.

Crystal data

C8H10N2O2F(000) = 704
Mr = 166.18Dx = 1.308 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2161 reflections
a = 13.1288 (8) Åθ = 3.3–20.5°
b = 7.5417 (4) ŵ = 0.10 mm1
c = 17.0734 (10) ÅT = 296 K
β = 92.857 (3)°Needle, colourless
V = 1688.40 (17) Å30.39 × 0.15 × 0.11 mm
Z = 8

Data collection

Bruker KAPPA APEXII CCD diffractometer4200 independent reflections
Radiation source: fine-focus sealed tube1708 reflections with I > 2σ(I)
graphiteRint = 0.066
ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −17→17
Tmin = 0.979, Tmax = 0.990k = −9→10
18386 measured reflectionsl = −22→22

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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 0.95w = 1/[σ2(Fo2) + (0.0499P)2] where P = (Fo2 + 2Fc2)/3
4200 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.22 e Å3

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.
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
O110.43146 (11)0.04300 (19)1.07269 (9)0.0607 (5)
O120.08143 (12)0.4522 (2)0.92286 (10)0.0767 (5)
N110.45156 (14)0.3134 (2)1.02178 (10)0.0459 (5)
H11N0.4261 (15)0.422 (3)1.0077 (12)0.055*
N120.55933 (15)0.3117 (2)1.02887 (13)0.0525 (5)
H12N0.5835 (16)0.216 (3)0.9985 (12)0.063*
H13N0.5782 (17)0.271 (3)1.0737 (13)0.063*
C110.28175 (15)0.1986 (2)1.03161 (12)0.0406 (5)
C120.23758 (16)0.3243 (3)0.98111 (12)0.0470 (6)
H120.27850.40090.95380.056*
C130.13289 (18)0.3352 (3)0.97163 (13)0.0532 (6)
C140.07247 (18)0.2229 (3)1.01231 (15)0.0646 (7)
H140.00180.23061.00590.078*
C150.11629 (19)0.0994 (3)1.06246 (15)0.0676 (7)
H150.07510.02451.09040.081*
C160.22077 (18)0.0856 (3)1.07168 (13)0.0545 (6)
H160.25000.00011.10490.065*
C170.39396 (16)0.1793 (3)1.04354 (12)0.0415 (5)
C180.1395 (2)0.5781 (4)0.88291 (17)0.0981 (11)
H18A0.17830.64900.92040.147*
H18B0.09460.65310.85160.147*
H18C0.18500.51770.84960.147*
O210.72052 (11)0.73719 (17)0.21668 (8)0.0534 (4)
O220.27188 (11)0.6456 (2)0.17438 (10)0.0692 (5)
N210.61560 (13)0.9272 (2)0.15351 (11)0.0471 (5)
H21N0.5565 (16)0.954 (3)0.1308 (12)0.057*
N220.69253 (15)1.0512 (3)0.13927 (12)0.0531 (6)
H23N0.7151 (16)1.092 (3)0.1850 (13)0.064*
H22N0.7419 (17)0.994 (3)0.1205 (14)0.064*
C210.54632 (15)0.6517 (2)0.20011 (11)0.0372 (5)
C220.44617 (16)0.7004 (3)0.18400 (12)0.0442 (5)
H220.43130.81470.16650.053*
C230.36779 (16)0.5814 (3)0.19354 (12)0.0460 (5)
C240.38825 (17)0.4133 (3)0.21999 (13)0.0553 (6)
H240.33570.33300.22680.066*
C250.48845 (19)0.3654 (3)0.23633 (14)0.0640 (7)
H250.50300.25140.25430.077*
C260.56714 (17)0.4813 (3)0.22674 (13)0.0523 (6)
H260.63410.44590.23800.063*
C270.63403 (16)0.7742 (3)0.19120 (11)0.0382 (5)
C280.18800 (17)0.5274 (3)0.17719 (16)0.0711 (8)
H28A0.20050.42470.14590.107*
H28B0.12720.58580.15710.107*
H28C0.17960.49190.23050.107*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O110.0571 (10)0.0390 (9)0.0842 (12)−0.0005 (8)−0.0140 (8)0.0216 (8)
O120.0586 (11)0.0935 (13)0.0778 (13)0.0257 (10)−0.0005 (9)0.0264 (10)
N110.0468 (12)0.0323 (10)0.0577 (12)0.0019 (9)−0.0059 (9)0.0088 (9)
N120.0491 (13)0.0412 (11)0.0660 (15)0.0008 (9)−0.0087 (10)0.0088 (10)
C110.0475 (13)0.0319 (11)0.0418 (13)0.0002 (10)−0.0044 (10)0.0006 (10)
C120.0478 (15)0.0476 (13)0.0459 (14)0.0062 (11)0.0042 (11)0.0032 (11)
C130.0547 (16)0.0549 (15)0.0498 (15)0.0110 (13)−0.0008 (12)0.0053 (12)
C140.0481 (15)0.0648 (17)0.0801 (19)−0.0026 (13)−0.0052 (14)0.0020 (14)
C150.0629 (18)0.0576 (17)0.082 (2)−0.0121 (13)0.0019 (14)0.0150 (14)
C160.0579 (16)0.0431 (13)0.0615 (16)−0.0066 (12)−0.0072 (12)0.0119 (11)
C170.0529 (14)0.0315 (12)0.0396 (13)−0.0005 (11)−0.0035 (10)0.0026 (10)
C180.091 (2)0.115 (3)0.091 (2)0.0472 (19)0.0296 (18)0.0613 (19)
O210.0428 (9)0.0515 (10)0.0644 (11)0.0025 (7)−0.0106 (8)0.0114 (7)
O220.0410 (10)0.0611 (11)0.1053 (14)0.0010 (8)0.0027 (9)0.0147 (9)
N210.0419 (11)0.0390 (11)0.0589 (13)−0.0055 (9)−0.0130 (9)0.0077 (9)
N220.0564 (14)0.0431 (12)0.0585 (14)−0.0114 (10)−0.0096 (11)0.0018 (10)
C210.0444 (13)0.0347 (12)0.0323 (12)0.0042 (10)−0.0003 (9)−0.0027 (9)
C220.0490 (14)0.0359 (12)0.0479 (14)0.0050 (11)0.0030 (11)0.0044 (10)
C230.0449 (14)0.0453 (13)0.0481 (14)0.0048 (11)0.0042 (11)−0.0009 (10)
C240.0577 (17)0.0415 (14)0.0666 (16)−0.0048 (11)0.0038 (13)0.0016 (12)
C250.0660 (18)0.0361 (13)0.089 (2)0.0054 (13)−0.0042 (14)0.0130 (12)
C260.0491 (14)0.0396 (13)0.0670 (16)0.0040 (11)−0.0073 (12)0.0050 (11)
C270.0451 (14)0.0350 (12)0.0339 (12)0.0035 (10)−0.0039 (10)−0.0040 (9)
C280.0483 (16)0.0705 (18)0.095 (2)−0.0070 (13)0.0064 (14)−0.0227 (15)

Geometric parameters (Å, °)

O11—C171.234 (2)O21—C271.228 (2)
O12—C131.368 (3)O22—C231.373 (2)
O12—C181.415 (3)O22—C281.419 (2)
N11—C171.327 (2)N21—C271.337 (2)
N11—N121.414 (2)N21—N221.407 (2)
N11—H11N0.91 (2)N21—H21N0.87 (2)
N12—H12N0.95 (2)N22—H23N0.88 (2)
N12—H13N0.85 (2)N22—H22N0.85 (2)
C11—C161.374 (3)C21—C221.380 (3)
C11—C121.389 (3)C21—C261.385 (3)
C11—C171.484 (3)C21—C271.490 (3)
C12—C131.378 (3)C22—C231.381 (3)
C12—H120.9300C22—H220.9300
C13—C141.372 (3)C23—C241.368 (3)
C14—C151.372 (3)C24—C251.379 (3)
C14—H140.9300C24—H240.9300
C15—C161.377 (3)C25—C261.369 (3)
C15—H150.9300C25—H250.9300
C16—H160.9300C26—H260.9300
C18—H18A0.9600C28—H28A0.9600
C18—H18B0.9600C28—H28B0.9600
C18—H18C0.9600C28—H28C0.9600
C13—O12—C18117.70 (18)C23—O22—C28118.35 (18)
C17—N11—N12123.42 (17)C27—N21—N22122.87 (18)
C17—N11—H11N123.5 (13)C27—N21—H21N123.3 (13)
N12—N11—H11N112.5 (13)N22—N21—H21N113.5 (13)
N11—N12—H12N108.7 (13)N21—N22—H23N107.0 (15)
N11—N12—H13N109.0 (15)N21—N22—H22N107.2 (15)
H12N—N12—H13N97.3 (19)H23N—N22—H22N106 (2)
C16—C11—C12119.8 (2)C22—C21—C26118.87 (19)
C16—C11—C17118.03 (18)C22—C21—C27123.24 (18)
C12—C11—C17122.19 (19)C26—C21—C27117.88 (18)
C13—C12—C11119.8 (2)C21—C22—C23120.78 (19)
C13—C12—H12120.1C21—C22—H22119.6
C11—C12—H12120.1C23—C22—H22119.6
O12—C13—C14115.2 (2)C24—C23—O22124.6 (2)
O12—C13—C12124.7 (2)C24—C23—C22120.4 (2)
C14—C13—C12120.1 (2)O22—C23—C22115.02 (19)
C15—C14—C13120.0 (2)C23—C24—C25118.6 (2)
C15—C14—H14120.0C23—C24—H24120.7
C13—C14—H14120.0C25—C24—H24120.7
C14—C15—C16120.5 (2)C26—C25—C24121.8 (2)
C14—C15—H15119.8C26—C25—H25119.1
C16—C15—H15119.8C24—C25—H25119.1
C11—C16—C15119.9 (2)C25—C26—C21119.6 (2)
C11—C16—H16120.1C25—C26—H26120.2
C15—C16—H16120.1C21—C26—H26120.2
O11—C17—N11121.8 (2)O21—C27—N21120.57 (19)
O11—C17—C11120.67 (18)O21—C27—C21121.92 (18)
N11—C17—C11117.55 (17)N21—C27—C21117.51 (18)
O12—C18—H18A109.5O22—C28—H28A109.5
O12—C18—H18B109.5O22—C28—H28B109.5
H18A—C18—H18B109.5H28A—C28—H28B109.5
O12—C18—H18C109.5O22—C28—H28C109.5
H18A—C18—H18C109.5H28A—C28—H28C109.5
H18B—C18—H18C109.5H28B—C28—H28C109.5
C16—C11—C12—C130.1 (3)C26—C21—C22—C23−0.5 (3)
C17—C11—C12—C13179.32 (18)C27—C21—C22—C23−179.80 (18)
C18—O12—C13—C14176.3 (2)C28—O22—C23—C24−4.2 (3)
C18—O12—C13—C12−4.0 (3)C28—O22—C23—C22175.51 (19)
C11—C12—C13—O12−179.2 (2)C21—C22—C23—C240.7 (3)
C11—C12—C13—C140.4 (3)C21—C22—C23—O22−179.05 (17)
O12—C13—C14—C15179.5 (2)O22—C23—C24—C25179.3 (2)
C12—C13—C14—C15−0.1 (4)C22—C23—C24—C25−0.4 (3)
C13—C14—C15—C16−0.8 (4)C23—C24—C25—C260.0 (3)
C12—C11—C16—C15−1.0 (3)C24—C25—C26—C210.1 (4)
C17—C11—C16—C15179.8 (2)C22—C21—C26—C250.1 (3)
C14—C15—C16—C111.3 (4)C27—C21—C26—C25179.42 (19)
N12—N11—C17—O110.9 (3)N22—N21—C27—O211.5 (3)
N12—N11—C17—C11−179.15 (17)N22—N21—C27—C21−178.00 (18)
C16—C11—C17—O1116.9 (3)C22—C21—C27—O21168.96 (19)
C12—C11—C17—O11−162.3 (2)C26—C21—C27—O21−10.3 (3)
C16—C11—C17—N11−163.0 (2)C22—C21—C27—N21−11.6 (3)
C12—C11—C17—N1117.8 (3)C26—C21—C27—N21169.15 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N11—H11N···N12i0.91 (2)2.12 (2)2.958 (2)153.3 (18)
N11—H11N···N11i0.91 (2)2.63 (2)3.191 (2)120.9 (13)
N12—H12N···O11ii0.95 (2)2.30 (2)3.193 (2)155.2 (18)
N12—H13N···N22iii0.85 (2)2.47 (2)3.185 (3)142.6 (19)
N21—H21N···O11iv0.87 (2)1.99 (2)2.860 (2)172 (2)
N22—H23N···O21v0.88 (2)2.14 (2)3.007 (2)168 (2)
C18—H18C···O21vi0.962.583.498 (3)160
C22—H22···O11iv0.932.353.208 (3)153
C26—H26···O21vii0.932.563.439 (3)157

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2; (iii) x, y−1, z+1; (iv) x, y+1, z−1; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+3/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2207).

References

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