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

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ISSN: 2056-9890

(E)-N′-[4-(Di­methyl­amino)­benzyl­­idene]-2-meth­­oxy­benzohydrazide

aCollege of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 18 June 2010; accepted 20 June 2010; online 26 June 2010)

In the title compound, C17H19N3O2, the two benzene rings form a dihedral angle of 89.2 (2)°. In the crystal structure, mol­ecules are linked through N—H⋯O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010[Hillmer, A. S., Putcha, P., Levin, J., Hogen, T., Hyman, B. T., Kretzschmar, H., McLean, P. J. & Giese, A. (2010). Biochem. Biophys. Res. Commun. 391, 461-466.]); Zhu et al. (2009[Zhu, Q.-Y., Wei, Y.-J. & Wang, F.-W. (2009). Pol. J. Chem. 83, 1233-1240.]); Jimenez-Pulido et al. (2008[Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677-1683.]); Raj et al. (2007[Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425-429.]); Zhong et al. (2007[Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774-3777.]). For hydrazones we have reported previously, see: Liu & You (2010a[Liu, S.-Y. & You, Z. (2010a). Acta Cryst. E66, o1652.],b[Liu, S.-Y. & You, Z. (2010b). Acta Cryst. E66, o1658.],c[Liu, S.-Y. & You, Z. (2010c). Acta Cryst. E66, o1662.]). For the crystal structures of similar hydrazone compounds, see: Khaledi et al. (2009[Khaledi, H., Saharin, S. M., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2009). Acta Cryst. E65, o1920.]); Warad et al. (2009[Warad, I., Al-Nuri, M., Al-Resayes, S., Al-Farhan, K. & Ghazzali, M. (2009). Acta Cryst. E65, o1597.]); Back et al. (2009[Back, D. F., Ballin, M. A. & de Oliveira, G. M. (2009). J. Mol. Struct. 935, 151-155.]); Vijayakumar et al. (2009[Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564-1569.]). For other related structures, see: Cao (2009[Cao, G.-B. (2009). Acta Cryst. E65, o2086.]); Xu et al. (2009[Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N3O2

  • Mr = 297.35

  • Orthorhombic, P b c a

  • a = 24.726 (4) Å

  • b = 15.385 (3) Å

  • c = 8.2700 (15) Å

  • V = 3146.0 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.20 × 0.17 × 0.13 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Version 2.03. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.983, Tmax = 0.989

  • 12277 measured reflections

  • 2096 independent reflections

  • 1545 reflections with I > 2σ(I)

  • Rint = 0.045

  • θmax = 22.7°

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.106

  • S = 1.04

  • 2096 reflections

  • 202 parameters

  • H-atom parameters constrained

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.90 2.03 2.914 (2) 165
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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


Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Zhu et al., 2009; Jimenez-Pulido et al., 2008; Raj et al., 2007; Zhong et al., 2007). The study on the crystal structures of such compounds is of particular interest (Khaledi et al., 2009; Warad et al., 2009; Back et al., 2009; Vijayakumar et al., 2009). As a continuation of our work on such compounds (Liu & You, 2010a,b,c), we report herein the crystal structure of the title new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the C1—C6 and C10—C15 benzene rings is 89.2 (2)°, indicating they are nearly perpendicular to each other. All the bond lengths are comparable to those observed in related structures (Cao, 2009; Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N—H···O hydrogen bonds, to form one-dimensional chains running along the c axis (Fig. 2 and Table 1).

Related literature top

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010); Zhu et al. (2009); Jimenez-Pulido et al. (2008); Raj et al. (2007); Zhong et al. (2007). For hydrazones we have reported previously, see: Liu & You (2010a,b,c). For the crystal structures of similar hydrazone compounds, see: Khaledi et al. (2009); Warad et al. (2009); Back et al. (2009); Vijayakumar et al. (2009). For other related structures, see: Cao (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 4-dimethylaminobenzaldehyde (0.05 mol, 7.5 g) and 2-methoxybenzohydrazide (0.05 mol, 8.3 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a period of 13 d.

Refinement top

H atoms were positioned geometrically and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

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. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.
(E)-N'-[4-(Dimethylamino)benzylidene]-2-methoxybenzohydrazide top
Crystal data top
C17H19N3O2Dx = 1.256 Mg m3
Mr = 297.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1881 reflections
a = 24.726 (4) Åθ = 2.5–24.0°
b = 15.385 (3) ŵ = 0.08 mm1
c = 8.2700 (15) ÅT = 298 K
V = 3146.0 (10) Å3Block, colourless
Z = 80.20 × 0.17 × 0.13 mm
F(000) = 1264
Data collection top
Bruker SMART CCD area-detector
diffractometer
2096 independent reflections
Radiation source: fine-focus sealed tube1545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 22.7°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2626
Tmin = 0.983, Tmax = 0.989k = 1316
12277 measured reflectionsl = 88
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2933P]
where P = (Fo2 + 2Fc2)/3
2096 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C17H19N3O2V = 3146.0 (10) Å3
Mr = 297.35Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 24.726 (4) ŵ = 0.08 mm1
b = 15.385 (3) ÅT = 298 K
c = 8.2700 (15) Å0.20 × 0.17 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2096 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1545 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.989Rint = 0.045
12277 measured reflectionsθmax = 22.7°
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.04Δρmax = 0.11 e Å3
2096 reflectionsΔρmin = 0.15 e Å3
202 parameters
Special details top

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) top
xyzUiso*/Ueq
O10.22678 (6)0.40089 (10)0.07729 (18)0.0681 (5)
O20.22007 (6)0.33552 (10)0.36694 (18)0.0635 (5)
N10.18746 (6)0.26778 (11)0.1458 (2)0.0497 (5)
H10.19510.24380.04910.060*
N20.14034 (6)0.24198 (11)0.2235 (2)0.0485 (5)
N30.07797 (7)0.02776 (13)0.3833 (2)0.0649 (5)
C10.27573 (9)0.37736 (13)0.0152 (3)0.0529 (6)
C20.27502 (8)0.33335 (12)0.1323 (2)0.0456 (5)
C30.32355 (9)0.30874 (14)0.2011 (3)0.0611 (6)
H30.32340.28080.30090.073*
C40.37239 (10)0.32468 (17)0.1251 (4)0.0754 (8)
H40.40470.30590.17070.090*
C50.37218 (11)0.36868 (17)0.0186 (4)0.0784 (8)
H50.40480.38050.06990.094*
C60.32491 (11)0.39565 (17)0.0884 (3)0.0700 (7)
H60.32580.42640.18520.084*
C70.22616 (11)0.44770 (17)0.2266 (3)0.0836 (8)
H7A0.24320.41340.30920.125*
H7B0.24540.50140.21380.125*
H7C0.18940.45970.25700.125*
C80.22464 (8)0.31366 (12)0.2249 (3)0.0454 (5)
C90.11475 (8)0.18206 (15)0.1511 (3)0.0511 (6)
H90.12860.16070.05450.061*
C100.06471 (8)0.14545 (13)0.2125 (2)0.0477 (5)
C110.04784 (8)0.06446 (15)0.1597 (3)0.0575 (6)
H110.06830.03590.08170.069*
C120.00212 (8)0.02449 (15)0.2177 (3)0.0595 (6)
H120.00700.03070.18080.071*
C130.03087 (8)0.06541 (14)0.3311 (2)0.0505 (6)
C140.01414 (8)0.14694 (15)0.3850 (3)0.0578 (6)
H140.03490.17590.46180.069*
C150.03229 (8)0.18573 (14)0.3275 (3)0.0559 (6)
H150.04210.24020.36660.067*
C160.09234 (10)0.05974 (17)0.3378 (3)0.0803 (8)
H16A0.06270.09810.36080.120*
H16B0.10040.06160.22430.120*
H16C0.12350.07780.39810.120*
C170.11115 (9)0.07019 (18)0.5026 (3)0.0823 (8)
H17A0.11810.12900.46960.124*
H17B0.09270.07030.60480.124*
H17C0.14480.03960.51310.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0796 (12)0.0712 (11)0.0536 (10)0.0085 (9)0.0061 (8)0.0234 (8)
O20.0784 (11)0.0708 (10)0.0414 (9)0.0189 (8)0.0174 (8)0.0065 (8)
N10.0541 (10)0.0541 (11)0.0409 (10)0.0082 (9)0.0165 (8)0.0036 (9)
N20.0496 (10)0.0499 (11)0.0459 (11)0.0043 (9)0.0139 (8)0.0023 (9)
N30.0521 (12)0.0772 (14)0.0653 (13)0.0155 (10)0.0051 (10)0.0058 (11)
C10.0655 (15)0.0453 (13)0.0479 (14)0.0098 (11)0.0155 (12)0.0028 (11)
C20.0550 (14)0.0359 (11)0.0458 (13)0.0035 (10)0.0138 (10)0.0035 (10)
C30.0631 (16)0.0563 (14)0.0639 (15)0.0020 (12)0.0095 (13)0.0019 (12)
C40.0549 (15)0.0767 (18)0.095 (2)0.0044 (13)0.0095 (14)0.0162 (17)
C50.0687 (18)0.0812 (19)0.085 (2)0.0273 (15)0.0342 (16)0.0231 (17)
C60.0837 (19)0.0681 (16)0.0581 (16)0.0265 (14)0.0266 (15)0.0032 (13)
C70.125 (2)0.0708 (17)0.0551 (16)0.0141 (16)0.0011 (15)0.0205 (14)
C80.0575 (13)0.0362 (11)0.0423 (13)0.0011 (10)0.0121 (11)0.0031 (10)
C90.0520 (13)0.0587 (14)0.0425 (13)0.0002 (11)0.0080 (10)0.0007 (11)
C100.0466 (12)0.0553 (14)0.0413 (12)0.0003 (10)0.0009 (10)0.0011 (11)
C110.0540 (14)0.0641 (15)0.0545 (14)0.0009 (12)0.0057 (11)0.0100 (12)
C120.0548 (14)0.0567 (14)0.0671 (16)0.0072 (12)0.0045 (12)0.0058 (12)
C130.0440 (12)0.0620 (15)0.0455 (13)0.0029 (11)0.0064 (10)0.0062 (12)
C140.0497 (13)0.0691 (16)0.0545 (14)0.0016 (12)0.0086 (11)0.0074 (12)
C150.0547 (13)0.0534 (13)0.0597 (14)0.0066 (11)0.0042 (11)0.0074 (12)
C160.0687 (16)0.0782 (19)0.0941 (19)0.0233 (14)0.0054 (14)0.0165 (16)
C170.0606 (15)0.114 (2)0.0728 (17)0.0136 (15)0.0145 (14)0.0077 (17)
Geometric parameters (Å, º) top
O1—C11.363 (2)C7—H7A0.9600
O1—C71.429 (3)C7—H7B0.9600
O2—C81.227 (2)C7—H7C0.9600
N1—C81.331 (2)C9—C101.451 (3)
N1—N21.389 (2)C9—H90.9300
N1—H10.9002C10—C111.385 (3)
N2—C91.269 (2)C10—C151.390 (3)
N3—C131.370 (3)C11—C121.373 (3)
N3—C171.440 (3)C11—H110.9300
N3—C161.442 (3)C12—C131.393 (3)
C1—C61.387 (3)C12—H120.9300
C1—C21.396 (3)C13—C141.394 (3)
C2—C31.381 (3)C14—C151.379 (3)
C2—C81.493 (3)C14—H140.9300
C3—C41.384 (3)C15—H150.9300
C3—H30.9300C16—H16A0.9600
C4—C51.367 (4)C16—H16B0.9600
C4—H40.9300C16—H16C0.9600
C5—C61.368 (4)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C1—O1—C7117.94 (17)N1—C8—C2115.55 (18)
C8—N1—N2120.22 (16)N2—C9—C10122.83 (19)
C8—N1—H1120.6N2—C9—H9118.6
N2—N1—H1118.0C10—C9—H9118.6
C9—N2—N1114.06 (16)C11—C10—C15116.31 (19)
C13—N3—C17120.6 (2)C11—C10—C9119.73 (19)
C13—N3—C16121.5 (2)C15—C10—C9123.93 (19)
C17—N3—C16117.47 (19)C12—C11—C10122.7 (2)
O1—C1—C6124.1 (2)C12—C11—H11118.6
O1—C1—C2116.54 (18)C10—C11—H11118.6
C6—C1—C2119.4 (2)C11—C12—C13121.0 (2)
C3—C2—C1118.84 (19)C11—C12—H12119.5
C3—C2—C8117.25 (19)C13—C12—H12119.5
C1—C2—C8123.87 (19)N3—C13—C12121.2 (2)
C2—C3—C4121.5 (2)N3—C13—C14122.1 (2)
C2—C3—H3119.2C12—C13—C14116.62 (19)
C4—C3—H3119.2C15—C14—C13121.8 (2)
C5—C4—C3118.6 (2)C15—C14—H14119.1
C5—C4—H4120.7C13—C14—H14119.1
C3—C4—H4120.7C14—C15—C10121.6 (2)
C4—C5—C6121.3 (2)C14—C15—H15119.2
C4—C5—H5119.3C10—C15—H15119.2
C6—C5—H5119.3N3—C16—H16A109.5
C5—C6—C1120.2 (2)N3—C16—H16B109.5
C5—C6—H6119.9H16A—C16—H16B109.5
C1—C6—H6119.9N3—C16—H16C109.5
O1—C7—H7A109.5H16A—C16—H16C109.5
O1—C7—H7B109.5H16B—C16—H16C109.5
H7A—C7—H7B109.5N3—C17—H17A109.5
O1—C7—H7C109.5N3—C17—H17B109.5
H7A—C7—H7C109.5H17A—C17—H17B109.5
H7B—C7—H7C109.5N3—C17—H17C109.5
O2—C8—N1123.55 (18)H17A—C17—H17C109.5
O2—C8—C2120.81 (19)H17B—C17—H17C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.902.032.914 (2)165
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC17H19N3O2
Mr297.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)24.726 (4), 15.385 (3), 8.2700 (15)
V3)3146.0 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.17 × 0.13
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.983, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
12277, 2096, 1545
Rint0.045
θmax (°)22.7
(sin θ/λ)max1)0.542
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.106, 1.04
No. of reflections2096
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 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
N1—H1···O2i0.902.032.914 (2)165.2
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

The authors acknowledge Taizhou University for financial support.

References

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