organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N′-[4-(Di­methyl­amino)­benzyl­­idene]-4-meth­oxybenzohydrazide

aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
*Correspondence e-mail: jiufulu@163.com

(Received 25 September 2008; accepted 25 September 2008; online 30 September 2008)

The title Schiff base compound, C17H19N3O2, was obtained from the condensation of 4-dimethyl­amino­benzaldehyde with 4-methoxy­benzohydrazide in an ethanol solution. The mol­ecule is twisted with respect to the N—N single bond [C—N—N—C = −159.27 (14)°] and the dihedral angle between the two aromatic rings is 67.1 (2)°. In the crystal structure, the mol­ecules are linked into chains along the c axis by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.],b[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.],c[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.]); Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]); He (2008[He, L. (2008). Acta Cryst. E64, o82.]); Shi et al. (2007[Shi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295-o1296.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N3O2

  • Mr = 297.35

  • Monoclinic, P 21 /c

  • a = 11.922 (4) Å

  • b = 13.224 (5) Å

  • c = 9.756 (4) Å

  • β = 91.469 (6)°

  • V = 1537.6 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.23 × 0.23 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.983

  • 8744 measured reflections

  • 3296 independent reflections

  • 2507 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.121

  • S = 1.03

  • 3296 reflections

  • 205 parameters

  • 1 restraint

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

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O1i 0.90 (1) 1.99 (1) 2.873 (2) 167 (2)
C7—H7⋯O1i 0.93 2.54 3.297 (2) 139
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report here the crystal structure of the title new Schiff base compound.

In the title molecule (Fig. 1), the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 67.1 (2)°, indicating that the molecule is twisted. The methoxy group is coplanar with the attached ring [C15—O2—C12—C13 = 0.8 (2)°]. The dimethylamino group is almost coplanar with the attached ring [C16—N3—C1—C2 = 3.8 (2)° and C17—N3—C1—C6 = 8.7 (3)°]. The C7–N1—N2—C8 torsion angle [-159.27 (14)°] indicates that the molecule is twisted about the N1—N2 bond.

In the crystal structure, the molecules are linked into chains (Fig. 2) running along the c axis by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Nie (2008); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 4-dimethylaminobenzaldehyde (0.1 mol) and 4-methoxybenzohydrazide (0.1 mol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a 95% ethanol solution at room temperature.

Refinement top

The imino H atom was located in a difference map and refined with a N—H distance restraint of 0.90 (1) Å and a fixed Uiso of 0.08 Å2. The other H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). A rotating group model was used for methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, showing N—H···O hydrogen-bonded (dashed lines) chains running along the c axis. C-bound H atoms have been omitted for clarity.
N'-[4-(Dimethylamino)benzylidene]-4-methoxybenzohydrazide top
Crystal data top
C17H19N3O2F(000) = 632
Mr = 297.35Dx = 1.284 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3161 reflections
a = 11.922 (4) Åθ = 2.5–27.2°
b = 13.224 (5) ŵ = 0.09 mm1
c = 9.756 (4) ÅT = 298 K
β = 91.469 (6)°Block, colourless
V = 1537.6 (10) Å30.23 × 0.23 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3296 independent reflections
Radiation source: fine-focus sealed tube2507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1414
Tmin = 0.981, Tmax = 0.983k = 1614
8744 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2298P]
where P = (Fo2 + 2Fc2)/3
3296 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C17H19N3O2V = 1537.6 (10) Å3
Mr = 297.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.922 (4) ŵ = 0.09 mm1
b = 13.224 (5) ÅT = 298 K
c = 9.756 (4) Å0.23 × 0.23 × 0.20 mm
β = 91.469 (6)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3296 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2507 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.983Rint = 0.020
8744 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.15 e Å3
3296 reflectionsΔρmin = 0.18 e Å3
205 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
N10.23023 (11)0.86331 (9)0.18617 (12)0.0451 (3)
N20.27424 (11)0.77478 (9)0.24111 (11)0.0441 (3)
N30.06781 (13)1.32361 (10)0.12512 (17)0.0665 (4)
O10.29961 (10)0.70488 (7)0.03342 (9)0.0520 (3)
O20.46299 (11)0.33676 (8)0.39093 (12)0.0612 (3)
C10.10930 (12)1.23056 (11)0.15842 (16)0.0473 (4)
C20.07206 (14)1.14376 (12)0.09023 (18)0.0552 (4)
H20.01811.14950.02010.066*
C30.11325 (14)1.05048 (11)0.12429 (17)0.0517 (4)
H30.08740.99430.07570.062*
C40.19240 (12)1.03716 (10)0.22919 (14)0.0428 (3)
C50.22870 (14)1.12314 (11)0.29766 (16)0.0523 (4)
H50.28091.11660.36960.063*
C60.19031 (14)1.21761 (12)0.26300 (17)0.0545 (4)
H60.21851.27380.30960.065*
C70.23746 (12)0.93903 (11)0.26614 (15)0.0440 (3)
H70.27300.93110.35140.053*
C80.30424 (12)0.69893 (10)0.15876 (13)0.0389 (3)
C90.34473 (11)0.60594 (10)0.22874 (13)0.0371 (3)
C100.41496 (13)0.54231 (11)0.15756 (14)0.0468 (4)
H100.43590.55970.06950.056*
C110.45393 (14)0.45430 (11)0.21489 (16)0.0506 (4)
H110.50180.41290.16610.061*
C120.42254 (13)0.42666 (10)0.34493 (15)0.0442 (3)
C130.35380 (13)0.48939 (11)0.41792 (14)0.0452 (3)
H130.33340.47190.50620.054*
C140.31545 (12)0.57821 (10)0.35951 (14)0.0421 (3)
H140.26890.62030.40910.051*
C150.43137 (17)0.30433 (13)0.52240 (19)0.0676 (5)
H15A0.45270.35460.58910.101*
H15B0.46830.24170.54440.101*
H15C0.35160.29470.52300.101*
C160.02077 (16)1.33522 (15)0.0240 (2)0.0727 (6)
H16A0.00881.32630.06580.109*
H16B0.05261.40160.03110.109*
H16C0.07781.28550.03910.109*
C170.1166 (2)1.41355 (13)0.1829 (2)0.0810 (6)
H17A0.11161.41150.28090.121*
H17B0.07681.47160.14810.121*
H17C0.19391.41780.15840.121*
H2A0.2875 (17)0.7721 (14)0.3316 (10)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0607 (8)0.0397 (6)0.0349 (6)0.0055 (5)0.0015 (5)0.0055 (5)
N20.0648 (8)0.0385 (6)0.0289 (6)0.0075 (6)0.0026 (5)0.0025 (5)
N30.0689 (10)0.0429 (7)0.0867 (11)0.0069 (7)0.0189 (8)0.0055 (7)
O10.0804 (8)0.0482 (6)0.0272 (5)0.0012 (5)0.0051 (5)0.0000 (4)
O20.0753 (8)0.0472 (6)0.0613 (7)0.0160 (5)0.0055 (6)0.0097 (5)
C10.0475 (8)0.0404 (8)0.0539 (9)0.0031 (6)0.0005 (7)0.0035 (7)
C20.0551 (9)0.0500 (9)0.0595 (10)0.0008 (7)0.0172 (8)0.0033 (7)
C30.0562 (9)0.0421 (8)0.0562 (10)0.0031 (7)0.0117 (7)0.0015 (7)
C40.0487 (8)0.0404 (7)0.0393 (7)0.0024 (6)0.0020 (6)0.0027 (6)
C50.0606 (10)0.0483 (9)0.0473 (9)0.0059 (7)0.0118 (7)0.0031 (7)
C60.0633 (10)0.0424 (8)0.0570 (10)0.0023 (7)0.0099 (8)0.0065 (7)
C70.0525 (8)0.0438 (8)0.0357 (7)0.0028 (6)0.0004 (6)0.0037 (6)
C80.0482 (8)0.0403 (7)0.0279 (7)0.0055 (6)0.0018 (5)0.0009 (5)
C90.0462 (7)0.0360 (7)0.0291 (6)0.0029 (6)0.0012 (5)0.0028 (5)
C100.0597 (9)0.0479 (8)0.0332 (7)0.0016 (7)0.0091 (6)0.0009 (6)
C110.0598 (9)0.0469 (8)0.0457 (8)0.0093 (7)0.0110 (7)0.0053 (7)
C120.0491 (8)0.0379 (7)0.0453 (8)0.0026 (6)0.0012 (6)0.0003 (6)
C130.0572 (9)0.0453 (8)0.0334 (7)0.0016 (7)0.0048 (6)0.0045 (6)
C140.0537 (8)0.0393 (7)0.0337 (7)0.0057 (6)0.0061 (6)0.0019 (6)
C150.0793 (12)0.0550 (10)0.0684 (12)0.0059 (9)0.0023 (9)0.0231 (9)
C160.0609 (11)0.0672 (11)0.0896 (15)0.0183 (9)0.0083 (10)0.0133 (10)
C170.1003 (16)0.0422 (9)0.0996 (16)0.0101 (10)0.0138 (13)0.0015 (10)
Geometric parameters (Å, º) top
N1—C71.2710 (18)C7—H70.93
N1—N21.3851 (16)C8—C91.4814 (19)
N2—C81.3395 (17)C9—C141.3810 (19)
N2—H2A0.893 (9)C9—C101.386 (2)
N3—C11.3624 (19)C10—C111.367 (2)
N3—C171.433 (2)C10—H100.93
N3—C161.435 (2)C11—C121.381 (2)
O1—C81.2252 (16)C11—H110.93
O2—C121.3550 (17)C12—C131.377 (2)
O2—C151.413 (2)C13—C141.3784 (19)
C1—C21.394 (2)C13—H130.93
C1—C61.397 (2)C14—H140.93
C2—C31.366 (2)C15—H15A0.96
C2—H20.93C15—H15B0.96
C3—C41.385 (2)C15—H15C0.96
C3—H30.93C16—H16A0.96
C4—C51.383 (2)C16—H16B0.96
C4—C71.447 (2)C16—H16C0.96
C5—C61.370 (2)C17—H17A0.96
C5—H50.93C17—H17B0.96
C6—H60.93C17—H17C0.96
C7—N1—N2114.15 (12)C10—C9—C8117.84 (12)
C8—N2—N1120.33 (11)C11—C10—C9121.00 (13)
C8—N2—H2A121.3 (13)C11—C10—H10119.5
N1—N2—H2A118.2 (13)C9—C10—H10119.5
C1—N3—C17120.98 (15)C10—C11—C12120.25 (14)
C1—N3—C16121.12 (15)C10—C11—H11119.9
C17—N3—C16117.75 (15)C12—C11—H11119.9
C12—O2—C15117.78 (13)O2—C12—C13124.65 (14)
N3—C1—C2121.39 (14)O2—C12—C11115.72 (13)
N3—C1—C6121.65 (14)C13—C12—C11119.63 (13)
C2—C1—C6116.96 (13)C12—C13—C14119.67 (13)
C3—C2—C1121.31 (14)C12—C13—H13120.2
C3—C2—H2119.3C14—C13—H13120.2
C1—C2—H2119.3C13—C14—C9121.28 (13)
C2—C3—C4121.90 (14)C13—C14—H14119.4
C2—C3—H3119.0C9—C14—H14119.4
C4—C3—H3119.0O2—C15—H15A109.5
C5—C4—C3116.82 (13)O2—C15—H15B109.5
C5—C4—C7120.51 (13)H15A—C15—H15B109.5
C3—C4—C7122.66 (13)O2—C15—H15C109.5
C6—C5—C4122.15 (15)H15A—C15—H15C109.5
C6—C5—H5118.9H15B—C15—H15C109.5
C4—C5—H5118.9N3—C16—H16A109.5
C5—C6—C1120.82 (15)N3—C16—H16B109.5
C5—C6—H6119.6H16A—C16—H16B109.5
C1—C6—H6119.6N3—C16—H16C109.5
N1—C7—C4122.33 (13)H16A—C16—H16C109.5
N1—C7—H7118.8H16B—C16—H16C109.5
C4—C7—H7118.8N3—C17—H17A109.5
O1—C8—N2123.01 (13)N3—C17—H17B109.5
O1—C8—C9121.27 (12)H17A—C17—H17B109.5
N2—C8—C9115.72 (11)N3—C17—H17C109.5
C14—C9—C10118.16 (13)H17A—C17—H17C109.5
C14—C9—C8124.00 (12)H17B—C17—H17C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.90 (1)1.99 (1)2.873 (2)167 (2)
C7—H7···O1i0.932.543.297 (2)139
Symmetry code: (i) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H19N3O2
Mr297.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.922 (4), 13.224 (5), 9.756 (4)
β (°) 91.469 (6)
V3)1537.6 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.23 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.981, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
8744, 3296, 2507
Rint0.020
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.03
No. of reflections3296
No. of parameters205
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.90 (1)1.99 (1)2.873 (2)167 (2)
C7—H7···O1i0.932.543.297 (2)139
Symmetry code: (i) x, y+3/2, z+1/2.
 

Acknowledgements

The author thanks the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

References

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First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHe, L. (2008). Acta Cryst. E64, o82.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295–o1296.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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