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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o876.
Published online 2009 March 28. doi:  10.1107/S1600536809010228
PMCID: PMC2968921

(E)-N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]-3-methoxy­benzohydrazide

Abstract

In the title compound, C16H16N2O3, the benzohydrazide group is not planar and the mol­ecule exists in a trans configuration with respect to the methyl­idene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the crystal structure, the mol­ecular packing is stabilized by intra­molecular O—H(...)N and inter­molecular N—H(...)O hydrogen bonds. The inter­molecular hydrogen bonding forms chains parallel to the b axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 [triangle]); Raj et al. (2007 [triangle]); Jimenez-Pulido et al. (2008 [triangle]). For related structures, see: Ban & Li (2008a [triangle],b [triangle]); Yehye et al. (2008 [triangle]); Fun et al. (2008a [triangle],b [triangle]); Yang et al. (2008 [triangle]); Ejsmont et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o876-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O3
  • M r = 284.31
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o876-efi1.jpg
  • a = 12.932 (2) Å
  • b = 8.756 (2) Å
  • c = 25.784 (3) Å
  • V = 2919.7 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.27 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.976, T max = 0.982
  • 22735 measured reflections
  • 3180 independent reflections
  • 2023 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.145
  • S = 1.01
  • 3180 reflections
  • 196 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXTL (Sheldrick, 2008 [triangle]); 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/S1600536809010228/bx2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010228/bx2198Isup2.hkl

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

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported two hydrazones (Ban & Li, 2008a,b). In this paper, we report herein the crystal structure of the title compound, (I). In the structure of (I), Fig. 1, the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the 3-methoxyphenyl unit, the methoxy group is nearly coplanar with the mean plane of the C10–C15 ring, with the C16 atom deviates from the plane by 0.024 (2) Å. The torsion angle of C7-N1-N2-C9 is 8.0 (3)°. In the crystal structure the molecular packing is stabilized by intramolecular O-H···N and intermolecular N—H···O hydrogen bonds, Table 1. The intermolecular hydrogen bond form chains parallel to the b axis, Fig. 2.

Experimental

The compound was prepared by refluxing 1-(2-hydroxyphenyl)ethanone (1.0 mol, 0136 g ) with 3-methoxybenzohydrazide (1.0 mol), 0166 g) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement

H2 was located in a difference Fourier map and refined isotropically, with N–H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions (C–H = 0.93 - 0.96 Å, O–H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and methyl C). A rotating group model was used for the methyl groups.

Figures

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

Crystal data

C16H16N2O3F(000) = 1200
Mr = 284.31Dx = 1.294 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2030 reflections
a = 12.932 (2) Åθ = 2.3–24.6°
b = 8.756 (2) ŵ = 0.09 mm1
c = 25.784 (3) ÅT = 298 K
V = 2919.7 (9) Å3Block, colourless
Z = 80.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer3180 independent reflections
Radiation source: fine-focus sealed tube2023 reflections with I > 2σ(I)
graphiteRint = 0.060
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.976, Tmax = 0.982k = −11→11
22735 measured reflectionsl = −32→32

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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0537P)2 + 0.9645P] where P = (Fo2 + 2Fc2)/3
3180 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.13 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 > 2sigma(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
O10.36951 (13)−0.23812 (18)0.55231 (7)0.0649 (5)
H10.3402−0.17160.56920.097*
O20.16810 (12)−0.08166 (16)0.63341 (7)0.0637 (5)
O3−0.13883 (13)0.2606 (3)0.68697 (8)0.0904 (7)
N10.35910 (13)−0.00001 (18)0.60790 (6)0.0449 (4)
N20.29750 (13)0.09206 (19)0.63821 (7)0.0455 (4)
C10.51395 (16)−0.0694 (2)0.56716 (8)0.0464 (5)
C20.46801 (19)−0.1972 (2)0.54406 (8)0.0531 (6)
C30.5262 (2)−0.2881 (3)0.51064 (10)0.0698 (7)
H30.4956−0.37290.49530.084*
C40.6267 (3)−0.2557 (3)0.49994 (11)0.0783 (9)
H40.6643−0.31890.47790.094*
C50.6727 (2)−0.1300 (3)0.52166 (10)0.0726 (8)
H50.7413−0.10670.51410.087*
C60.61702 (17)−0.0388 (3)0.55467 (9)0.0605 (6)
H60.64890.04620.56920.073*
C70.45502 (16)0.0315 (2)0.60247 (8)0.0460 (5)
C80.50836 (18)0.1605 (3)0.62968 (11)0.0736 (8)
H8A0.51150.24750.60710.110*
H8B0.57720.12990.63890.110*
H8C0.47060.18670.66050.110*
C90.20029 (16)0.0434 (2)0.64786 (8)0.0453 (5)
C100.13506 (15)0.1510 (2)0.67804 (7)0.0416 (5)
C110.02940 (15)0.1511 (2)0.66810 (8)0.0472 (5)
H110.00200.08460.64360.057*
C12−0.03443 (18)0.2490 (3)0.69451 (9)0.0587 (6)
C130.0058 (2)0.3454 (3)0.73150 (10)0.0744 (8)
H13−0.03750.41170.74940.089*
C140.1094 (2)0.3437 (3)0.74187 (10)0.0741 (8)
H140.13610.40870.76710.089*
C150.17528 (17)0.2464 (3)0.71537 (9)0.0551 (6)
H150.24570.24540.72270.066*
C16−0.1850 (2)0.1657 (4)0.64939 (12)0.0932 (10)
H16A−0.15430.18530.61620.140*
H16B−0.25780.18650.64780.140*
H16C−0.17430.06070.65860.140*
H20.3118 (19)0.1919 (13)0.6414 (10)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0719 (12)0.0497 (10)0.0731 (12)−0.0087 (9)−0.0043 (9)−0.0107 (8)
O20.0519 (9)0.0352 (8)0.1039 (13)−0.0034 (7)−0.0095 (9)−0.0069 (8)
O30.0454 (10)0.1393 (19)0.0865 (14)0.0128 (11)0.0099 (10)−0.0058 (13)
N10.0432 (10)0.0389 (9)0.0524 (10)0.0035 (8)−0.0032 (8)−0.0017 (8)
N20.0426 (10)0.0339 (9)0.0602 (11)0.0017 (8)0.0002 (8)−0.0049 (9)
C10.0512 (13)0.0411 (12)0.0468 (12)0.0051 (10)−0.0031 (10)0.0027 (9)
C20.0687 (16)0.0415 (13)0.0490 (13)0.0059 (11)−0.0025 (11)0.0042 (10)
C30.104 (2)0.0451 (15)0.0607 (16)0.0093 (14)0.0061 (15)−0.0058 (12)
C40.101 (2)0.0675 (18)0.0664 (17)0.0287 (17)0.0235 (16)0.0042 (14)
C50.0695 (17)0.0764 (19)0.0720 (17)0.0163 (15)0.0202 (14)0.0064 (15)
C60.0561 (15)0.0587 (15)0.0666 (15)0.0054 (12)0.0031 (12)0.0024 (12)
C70.0440 (12)0.0407 (11)0.0534 (13)0.0070 (9)−0.0078 (10)−0.0012 (10)
C80.0466 (14)0.0697 (17)0.105 (2)0.0040 (12)−0.0096 (14)−0.0346 (16)
C90.0429 (12)0.0363 (11)0.0567 (13)0.0008 (9)−0.0096 (10)0.0052 (10)
C100.0436 (11)0.0387 (11)0.0427 (11)−0.0043 (9)−0.0015 (9)0.0073 (9)
C110.0445 (12)0.0505 (13)0.0466 (12)−0.0060 (10)0.0016 (10)0.0068 (10)
C120.0467 (14)0.0763 (17)0.0531 (14)0.0014 (12)0.0097 (11)0.0084 (13)
C130.0687 (18)0.094 (2)0.0608 (16)0.0095 (15)0.0184 (14)−0.0177 (15)
C140.0771 (19)0.092 (2)0.0529 (15)−0.0094 (16)0.0051 (13)−0.0249 (14)
C150.0464 (12)0.0690 (15)0.0498 (13)−0.0057 (11)−0.0005 (10)−0.0029 (12)
C160.0430 (15)0.140 (3)0.097 (2)−0.0071 (16)−0.0068 (15)0.012 (2)

Geometric parameters (Å, °)

O1—C21.340 (3)C6—H60.9300
O1—H10.8200C7—C81.498 (3)
O2—C91.229 (2)C8—H8A0.9600
O3—C121.368 (3)C8—H8B0.9600
O3—C161.409 (4)C8—H8C0.9600
N1—C71.278 (2)C9—C101.485 (3)
N1—N21.377 (2)C10—C151.376 (3)
N2—C91.351 (3)C10—C111.390 (3)
N2—H20.897 (10)C11—C121.371 (3)
C1—C61.397 (3)C11—H110.9300
C1—C21.401 (3)C12—C131.376 (3)
C1—C71.480 (3)C13—C141.367 (4)
C2—C31.394 (3)C13—H130.9300
C3—C41.358 (4)C14—C151.385 (3)
C3—H30.9300C14—H140.9300
C4—C51.371 (4)C15—H150.9300
C4—H40.9300C16—H16A0.9600
C5—C61.372 (3)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C2—O1—H1109.5C7—C8—H8C109.5
C12—O3—C16118.2 (2)H8A—C8—H8C109.5
C7—N1—N2119.81 (17)H8B—C8—H8C109.5
C9—N2—N1117.28 (17)O2—C9—N2122.7 (2)
C9—N2—H2118.8 (16)O2—C9—C10122.1 (2)
N1—N2—H2120.2 (17)N2—C9—C10115.14 (18)
C6—C1—C2117.4 (2)C15—C10—C11120.0 (2)
C6—C1—C7121.3 (2)C15—C10—C9122.46 (19)
C2—C1—C7121.4 (2)C11—C10—C9117.50 (18)
O1—C2—C3117.3 (2)C12—C11—C10120.0 (2)
O1—C2—C1123.3 (2)C12—C11—H11120.0
C3—C2—C1119.3 (2)C10—C11—H11120.0
C4—C3—C2121.6 (3)O3—C12—C11124.7 (2)
C4—C3—H3119.2O3—C12—C13115.2 (2)
C2—C3—H3119.2C11—C12—C13120.0 (2)
C3—C4—C5120.0 (3)C14—C13—C12120.0 (2)
C3—C4—H4120.0C14—C13—H13120.0
C5—C4—H4120.0C12—C13—H13120.0
C4—C5—C6119.5 (3)C13—C14—C15120.9 (2)
C4—C5—H5120.2C13—C14—H14119.6
C6—C5—H5120.2C15—C14—H14119.6
C5—C6—C1122.2 (2)C10—C15—C14119.1 (2)
C5—C6—H6118.9C10—C15—H15120.5
C1—C6—H6118.9C14—C15—H15120.5
N1—C7—C1115.99 (19)O3—C16—H16A109.5
N1—C7—C8123.94 (19)O3—C16—H16B109.5
C1—C7—C8120.07 (19)H16A—C16—H16B109.5
C7—C8—H8A109.5O3—C16—H16C109.5
C7—C8—H8B109.5H16A—C16—H16C109.5
H8A—C8—H8B109.5H16B—C16—H16C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)2.01 (1)2.894 (2)168 (2)
O1—H1···N10.821.822.534 (2)145

Symmetry codes: (i) −x+1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2198).

References

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