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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 65| Part 11| November 2009| Page o2645
https://doi.org/10.1107/S1600536809039713

(E)-2-Meth­­oxy-N′-(4-meth­oxy­benzyl­­idene)benzohydrazide

Guo-Biao Caoa*

aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
*Correspondence e-mail: guobiao_cao@126.com

(Received 21 September 2009; accepted 29 September 2009; online 3 October 2009)

The mol­ecule of the title compound, C16H16N2O3, displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189.]); Fun et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]); Li & Ban (2009[Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o1466.]); Zhu et al. (2009[Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.]); Yang (2007[Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343-348.]); You et al. (2008[You, Z.-L., Dai, W.-M., Xu, X.-Q. & Hu, Y.-Q. (2008). Pol. J. Chem. 82, 2215-2219.]). For the hydrazone compounds we have reported previously, see: Qu et al. (2008[Qu, L.-Z., Yang, T., Cao, G.-B. & Wang, X.-Y. (2008). Acta Cryst. E64, o2061.]); Yang et al. (2008[Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.]); Cao & Lu (2009a[Cao, G.-B. & Lu, X.-H. (2009a). Acta Cryst. E65, o1587.],b[Cao, G.-B. & Lu, X.-H. (2009b). Acta Cryst. E65, o1600.]); Qu & Cao (2009[Qu, L.-Z. & Cao, G.-B. (2009). Acta Cryst. E65, o1705.]); Cao & Wang (2009[Cao, G.-B. & Wang, X.-Y. (2009). Acta Cryst. E65, o1725.]).

[Scheme 1]

Experimental

Crystal data

  • C16H16N2O3

  • Mr = 284.31

  • Orthorhombic, P b c a

  • a = 14.990 (1) Å

  • b = 8.076 (1) Å

  • c = 24.122 (2) Å

  • V = 2920.2 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.17 × 0.15 × 0.15 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.987

  • 16039 measured reflections

  • 3011 independent reflections

  • 1225 reflections with I > 2σ(I)

  • Rint = 0.117
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.149

  • S = 0.92

  • 3011 reflections

  • 196 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 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
N2—H2A⋯O2i 0.899 (10) 2.093 (15) 2.940 (3) 157 (3)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

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/S1600536809039713/rz2367sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039713/rz2367Isup2.hkl

checkCIF report


Comment top

Study on the crystal structures of hydrazone derivatives is an interesting topic in structural chemistry. Recently, the crystal structures of a number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b; Qu & Cao, 2009; Cao & Wang, 2009), the title new hydrazone compound, derived from the reaction of 4-methoxybenzaldehyde with an equimolar quantity of 2-methoxybenzohydrazide, is reported.

The molecule of the title compound (Fig. 1) displays an E configuration about the C═N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the b axis (Fig. 2).

Related literature top

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For the hydrazone compounds we have reported previously, see: Qu et al. (2008); Yang et al. (2008); Cao & Lu (2009a,b); Qu & Cao (2009); Cao & Wang (2009).

Experimental top

The title compound was prepared by refluxing 4-methoxybenzaldehyde (0.1 mmol, 13.6 mg) with 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) in methanol (20 ml). Colourless block-like crystals were formed by slow evaporation of the solution in air.

Refinement top

H2A 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 placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93-0.96 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(methyl C).

Structure description top

Study on the crystal structures of hydrazone derivatives is an interesting topic in structural chemistry. Recently, the crystal structures of a number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b; Qu & Cao, 2009; Cao & Wang, 2009), the title new hydrazone compound, derived from the reaction of 4-methoxybenzaldehyde with an equimolar quantity of 2-methoxybenzohydrazide, is reported.

The molecule of the title compound (Fig. 1) displays an E configuration about the C═N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the b axis (Fig. 2).

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For the hydrazone compounds we have reported previously, see: Qu et al. (2008); Yang et al. (2008); Cao & Lu (2009a,b); Qu & Cao (2009); Cao & Wang (2009).

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 the title compound with ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines.
(E)-2-Methoxy-N'-(4-methoxybenzylidene)benzohydrazide top
Crystal data top
C16H16N2O3F(000) = 1200
Mr = 284.31Dx = 1.293 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 687 reflections
a = 14.990 (1) Åθ = 2.6–24.5°
b = 8.076 (1) ŵ = 0.09 mm−1
c = 24.122 (2) ÅT = 298 K
V = 2920.2 (5) Å3Block, colourless
Z = 80.17 × 0.15 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3011 independent reflections
Radiation source: fine-focus sealed tube1225 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.117
ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −18→14
Tmin = 0.985, Tmax = 0.987k = −10→9
16039 measured reflectionsl = −29→30
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0609P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max = 0.001
3011 reflectionsΔρmax = 0.17 e Å−3
196 parametersΔρmin = −0.15 e Å−3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0064 (9)
Crystal data top
C16H16N2O3V = 2920.2 (5) Å3
Mr = 284.31Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.990 (1) ŵ = 0.09 mm−1
b = 8.076 (1) ÅT = 298 K
c = 24.122 (2) Å0.17 × 0.15 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3011 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1225 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.987Rint = 0.117
16039 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.17 e Å−3
3011 reflectionsΔρmin = −0.15 e Å−3
196 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 > 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) top
xyzUiso*/Ueq
N10.24763 (16)0.2770 (3)0.63202 (9)0.0545 (7)
N20.22280 (16)0.3524 (3)0.68158 (10)0.0538 (7)
O10.44582 (16)0.0703 (3)0.41056 (8)0.0775 (7)
O20.15343 (14)0.1210 (3)0.71066 (8)0.0674 (6)
O30.12187 (13)0.6010 (3)0.73232 (9)0.0704 (7)
C10.3439 (2)0.2823 (3)0.55389 (11)0.0513 (8)
C20.2946 (2)0.1755 (4)0.52098 (12)0.0596 (9)
H20.23640.14930.53100.072*
C30.3305 (2)0.1079 (4)0.47389 (13)0.0629 (9)
H30.29620.03740.45210.076*
C40.4177 (2)0.1438 (4)0.45845 (12)0.0591 (9)
C50.4675 (2)0.2488 (4)0.49037 (12)0.0638 (9)
H50.52600.27320.48060.077*
C60.4299 (2)0.3188 (4)0.53754 (12)0.0628 (9)
H60.46370.39210.55860.075*
C70.5366 (2)0.0952 (5)0.39380 (14)0.0938 (12)
H7A0.54680.21090.38730.141*
H7B0.54800.03420.36040.141*
H7C0.57590.05710.42250.141*
C80.3105 (2)0.3490 (4)0.60596 (12)0.0565 (8)
H80.33530.44530.62040.068*
C90.17680 (19)0.2648 (4)0.71898 (12)0.0518 (8)
C100.15877 (18)0.3466 (3)0.77329 (11)0.0473 (7)
C110.13233 (17)0.5107 (4)0.77954 (13)0.0518 (8)
C120.11833 (19)0.5735 (4)0.83241 (14)0.0632 (9)
H120.10210.68380.83700.076*
C130.1284 (2)0.4732 (5)0.87795 (14)0.0754 (10)
H130.11970.51700.91320.091*
C140.1508 (2)0.3111 (5)0.87232 (14)0.0771 (10)
H140.15600.24320.90330.092*
C150.1658 (2)0.2486 (4)0.81986 (13)0.0636 (9)
H150.18110.13760.81590.076*
C160.0725 (2)0.7525 (4)0.73634 (14)0.0903 (12)
H16A0.01780.73280.75590.135*
H16B0.05950.79290.69980.135*
H16C0.10730.83320.75600.135*
H2A0.2470 (19)0.452 (2)0.6882 (13)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0619 (17)0.0495 (16)0.0521 (15)0.0013 (13)0.0033 (13)−0.0108 (13)
N20.0596 (17)0.0448 (16)0.0572 (15)−0.0048 (13)0.0059 (13)−0.0116 (14)
O10.0876 (18)0.0791 (17)0.0657 (14)0.0123 (13)0.0205 (13)−0.0048 (12)
O20.0754 (15)0.0436 (14)0.0831 (15)−0.0082 (11)0.0145 (12)−0.0180 (12)
O30.0831 (16)0.0475 (13)0.0806 (15)0.0149 (11)0.0209 (13)0.0047 (12)
C10.058 (2)0.0453 (18)0.0505 (17)0.0018 (15)−0.0028 (15)0.0002 (15)
C20.055 (2)0.064 (2)0.0597 (19)−0.0010 (16)0.0036 (16)−0.0066 (17)
C30.064 (2)0.066 (2)0.0587 (19)−0.0018 (17)−0.0036 (17)−0.0125 (17)
C40.071 (2)0.052 (2)0.0545 (19)0.0117 (17)0.0061 (17)0.0034 (16)
C50.062 (2)0.063 (2)0.067 (2)−0.0049 (17)0.0077 (18)0.0079 (18)
C60.068 (2)0.060 (2)0.060 (2)−0.0112 (17)−0.0024 (17)−0.0026 (17)
C70.089 (3)0.108 (3)0.085 (2)0.030 (2)0.036 (2)0.014 (2)
C80.067 (2)0.0452 (19)0.0571 (19)−0.0020 (16)−0.0020 (17)−0.0046 (16)
C90.0468 (18)0.0441 (19)0.065 (2)0.0042 (15)0.0003 (15)−0.0089 (17)
C100.0449 (17)0.0409 (18)0.0560 (18)0.0016 (13)0.0002 (14)−0.0063 (15)
C110.0481 (19)0.0448 (19)0.062 (2)−0.0015 (14)0.0059 (15)−0.0028 (16)
C120.058 (2)0.054 (2)0.078 (2)0.0001 (15)0.0160 (18)−0.0192 (19)
C130.082 (3)0.080 (3)0.064 (2)−0.004 (2)0.0088 (19)−0.018 (2)
C140.092 (3)0.077 (3)0.062 (2)0.013 (2)0.0017 (19)0.002 (2)
C150.071 (2)0.053 (2)0.067 (2)0.0123 (17)0.0026 (17)−0.0045 (18)
C160.089 (3)0.057 (2)0.124 (3)0.031 (2)0.033 (2)0.016 (2)
Geometric parameters (Å, º) top
N1—C81.273 (3)C6—H60.9300
N1—N21.392 (3)C7—H7A0.9600
N2—C91.338 (3)C7—H7B0.9600
N2—H2A0.899 (10)C7—H7C0.9600
O1—C41.366 (3)C8—H80.9300
O1—C71.434 (4)C9—C101.492 (4)
O2—C91.230 (3)C10—C151.378 (4)
O3—C111.362 (3)C10—C111.391 (4)
O3—C161.432 (3)C11—C121.388 (4)
C1—C61.381 (4)C12—C131.373 (4)
C1—C21.386 (4)C12—H120.9300
C1—C81.455 (4)C13—C141.359 (5)
C2—C31.370 (4)C13—H130.9300
C2—H20.9300C14—C151.381 (4)
C3—C41.390 (4)C14—H140.9300
C3—H30.9300C15—H150.9300
C4—C51.367 (4)C16—H16A0.9600
C5—C61.390 (4)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
C8—N1—N2115.0 (2)N1—C8—C1120.8 (3)
C9—N2—N1119.1 (2)N1—C8—H8119.6
C9—N2—H2A124 (2)C1—C8—H8119.6
N1—N2—H2A116 (2)O2—C9—N2122.4 (3)
C4—O1—C7118.1 (3)O2—C9—C10120.7 (3)
C11—O3—C16117.4 (2)N2—C9—C10116.9 (3)
C6—C1—C2117.8 (3)C15—C10—C11118.7 (3)
C6—C1—C8119.3 (3)C15—C10—C9116.6 (3)
C2—C1—C8122.8 (3)C11—C10—C9124.6 (3)
C3—C2—C1120.9 (3)O3—C11—C12123.7 (3)
C3—C2—H2119.5O3—C11—C10116.9 (3)
C1—C2—H2119.5C12—C11—C10119.4 (3)
C2—C3—C4120.5 (3)C13—C12—C11120.2 (3)
C2—C3—H3119.7C13—C12—H12119.9
C4—C3—H3119.7C11—C12—H12119.9
O1—C4—C5125.3 (3)C14—C13—C12121.0 (3)
O1—C4—C3115.3 (3)C14—C13—H13119.5
C5—C4—C3119.5 (3)C12—C13—H13119.5
C4—C5—C6119.5 (3)C13—C14—C15119.0 (3)
C4—C5—H5120.2C13—C14—H14120.5
C6—C5—H5120.2C15—C14—H14120.5
C1—C6—C5121.7 (3)C10—C15—C14121.6 (3)
C1—C6—H6119.2C10—C15—H15119.2
C5—C6—H6119.2C14—C15—H15119.2
O1—C7—H7A109.5O3—C16—H16A109.5
O1—C7—H7B109.5O3—C16—H16B109.5
H7A—C7—H7B109.5H16A—C16—H16B109.5
O1—C7—H7C109.5O3—C16—H16C109.5
H7A—C7—H7C109.5H16A—C16—H16C109.5
H7B—C7—H7C109.5H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.90 (1)2.09 (2)2.940 (3)157 (3)
Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC16H16N2O3
Mr284.31
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)14.990 (1), 8.076 (1), 24.122 (2)
V (Å3)2920.2 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.17 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.985, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		16039, 3011, 1225
Rint0.117
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.149, 0.92
No. of reflections3011
No. of parameters196
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.17, −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
N2—H2A···O2i0.899 (10)2.093 (15)2.940 (3)157 (3)
Symmetry code: (i) −x+1/2, y+1/2, z.
 

Acknowledgements

The vital foundation of Ankang University (project No. 2008AKXY012), and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

References

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2645
https://doi.org/10.1107/S1600536809039713
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