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

Lu, J.-F.

doi:10.1107/S1600536808031012

organic compounds

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Volume 64| Part 10| October 2008| Page o2033

doi:10.1107/S1600536808031012

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

Jiu-Fu Lu ^a ^*

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

Experimental

Crystal data

C₁₇H₁₉N₃O₂
M_r = 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 ) T_min = 0.981, T_max = 0.983
8744 measured reflections
3296 independent reflections
2507 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031012/ci2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031012/ci2684Isup2.hkl

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	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

C₁₇H₁₉N₃O₂	F(000) = 632
M_r = 297.35	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3161 reflections
a = 11.922 (4) Å	θ = 2.5–27.2°
b = 13.224 (5) Å	µ = 0.09 mm⁻¹
c = 9.756 (4) Å	T = 298 K
β = 91.469 (6)°	Block, colourless
V = 1537.6 (10) Å³	0.23 × 0.23 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3296 independent reflections
Radiation source: fine-focus sealed tube	2507 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
T_min = 0.981, T_max = 0.983	k = −16→14
8744 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0597P)² + 0.2298P] where P = (F_o² + 2F_c²)/3
3296 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O₂	V = 1537.6 (10) Å³
M_r = 297.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.922 (4) Å	µ = 0.09 mm⁻¹
b = 13.224 (5) Å	T = 298 K
c = 9.756 (4) Å	0.23 × 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)
T_min = 0.981, T_max = 0.983	R_int = 0.020
8744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.15 e Å⁻³
3296 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1	0.23023 (11)	0.86331 (9)	0.18617 (12)	0.0451 (3)
N2	0.27424 (11)	0.77478 (9)	0.24111 (11)	0.0441 (3)
N3	0.06781 (13)	1.32361 (10)	0.12512 (17)	0.0665 (4)
O1	0.29961 (10)	0.70488 (7)	0.03342 (9)	0.0520 (3)
O2	0.46299 (11)	0.33676 (8)	0.39093 (12)	0.0612 (3)
C1	0.10930 (12)	1.23056 (11)	0.15842 (16)	0.0473 (4)
C2	0.07206 (14)	1.14376 (12)	0.09023 (18)	0.0552 (4)
H2	0.0181	1.1495	0.0201	0.066*
C3	0.11325 (14)	1.05048 (11)	0.12429 (17)	0.0517 (4)
H3	0.0874	0.9943	0.0757	0.062*
C4	0.19240 (12)	1.03716 (10)	0.22919 (14)	0.0428 (3)
C5	0.22870 (14)	1.12314 (11)	0.29766 (16)	0.0523 (4)
H5	0.2809	1.1166	0.3696	0.063*
C6	0.19031 (14)	1.21761 (12)	0.26300 (17)	0.0545 (4)
H6	0.2185	1.2738	0.3096	0.065*
C7	0.23746 (12)	0.93903 (11)	0.26614 (15)	0.0440 (3)
H7	0.2730	0.9311	0.3514	0.053*
C8	0.30424 (12)	0.69893 (10)	0.15876 (13)	0.0389 (3)
C9	0.34473 (11)	0.60594 (10)	0.22874 (13)	0.0371 (3)
C10	0.41496 (13)	0.54231 (11)	0.15756 (14)	0.0468 (4)
H10	0.4359	0.5597	0.0695	0.056*
C11	0.45393 (14)	0.45430 (11)	0.21489 (16)	0.0506 (4)
H11	0.5018	0.4129	0.1661	0.061*
C12	0.42254 (13)	0.42666 (10)	0.34493 (15)	0.0442 (3)
C13	0.35380 (13)	0.48939 (11)	0.41792 (14)	0.0452 (3)
H13	0.3334	0.4719	0.5062	0.054*
C14	0.31545 (12)	0.57821 (10)	0.35951 (14)	0.0421 (3)
H14	0.2689	0.6203	0.4091	0.051*
C15	0.43137 (17)	0.30433 (13)	0.52240 (19)	0.0676 (5)
H15A	0.4527	0.3546	0.5891	0.101*
H15B	0.4683	0.2417	0.5444	0.101*
H15C	0.3516	0.2947	0.5230	0.101*
C16	−0.02077 (16)	1.33522 (15)	0.0240 (2)	0.0727 (6)
H16A	0.0088	1.3263	−0.0658	0.109*
H16B	−0.0526	1.4016	0.0311	0.109*
H16C	−0.0778	1.2855	0.0391	0.109*
C17	0.1166 (2)	1.41355 (13)	0.1829 (2)	0.0810 (6)
H17A	0.1116	1.4115	0.2809	0.121*
H17B	0.0768	1.4716	0.1481	0.121*
H17C	0.1939	1.4178	0.1584	0.121*
H2A	0.2875 (17)	0.7721 (14)	0.3316 (10)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0607 (8)	0.0397 (6)	0.0349 (6)	0.0055 (5)	−0.0015 (5)	0.0055 (5)
N2	0.0648 (8)	0.0385 (6)	0.0289 (6)	0.0075 (6)	−0.0026 (5)	0.0025 (5)
N3	0.0689 (10)	0.0429 (7)	0.0867 (11)	0.0069 (7)	−0.0189 (8)	0.0055 (7)
O1	0.0804 (8)	0.0482 (6)	0.0272 (5)	−0.0012 (5)	−0.0051 (5)	0.0000 (4)
O2	0.0753 (8)	0.0472 (6)	0.0613 (7)	0.0160 (5)	0.0055 (6)	0.0097 (5)
C1	0.0475 (8)	0.0404 (8)	0.0539 (9)	0.0031 (6)	0.0005 (7)	0.0035 (7)
C2	0.0551 (9)	0.0500 (9)	0.0595 (10)	−0.0008 (7)	−0.0172 (8)	0.0033 (7)
C3	0.0562 (9)	0.0421 (8)	0.0562 (10)	−0.0031 (7)	−0.0117 (7)	−0.0015 (7)
C4	0.0487 (8)	0.0404 (7)	0.0393 (7)	0.0024 (6)	0.0020 (6)	0.0027 (6)
C5	0.0606 (10)	0.0483 (9)	0.0473 (9)	0.0059 (7)	−0.0118 (7)	−0.0031 (7)
C6	0.0633 (10)	0.0424 (8)	0.0570 (10)	0.0023 (7)	−0.0099 (8)	−0.0065 (7)
C7	0.0525 (8)	0.0438 (8)	0.0357 (7)	0.0028 (6)	−0.0004 (6)	0.0037 (6)
C8	0.0482 (8)	0.0403 (7)	0.0279 (7)	−0.0055 (6)	−0.0018 (5)	−0.0009 (5)
C9	0.0462 (7)	0.0360 (7)	0.0291 (6)	−0.0029 (6)	−0.0012 (5)	−0.0028 (5)
C10	0.0597 (9)	0.0479 (8)	0.0332 (7)	0.0016 (7)	0.0091 (6)	−0.0009 (6)
C11	0.0598 (9)	0.0469 (8)	0.0457 (8)	0.0093 (7)	0.0110 (7)	−0.0053 (7)
C12	0.0491 (8)	0.0379 (7)	0.0453 (8)	0.0026 (6)	−0.0012 (6)	0.0003 (6)
C13	0.0572 (9)	0.0453 (8)	0.0334 (7)	0.0016 (7)	0.0048 (6)	0.0045 (6)
C14	0.0537 (8)	0.0393 (7)	0.0337 (7)	0.0057 (6)	0.0061 (6)	−0.0019 (6)
C15	0.0793 (12)	0.0550 (10)	0.0684 (12)	0.0059 (9)	−0.0023 (9)	0.0231 (9)
C16	0.0609 (11)	0.0672 (11)	0.0896 (15)	0.0183 (9)	−0.0083 (10)	0.0133 (10)
C17	0.1003 (16)	0.0422 (9)	0.0996 (16)	0.0101 (10)	−0.0138 (13)	−0.0015 (10)

Geometric parameters (Å, º) top

N1—C7	1.2710 (18)	C7—H7	0.93
N1—N2	1.3851 (16)	C8—C9	1.4814 (19)
N2—C8	1.3395 (17)	C9—C14	1.3810 (19)
N2—H2A	0.893 (9)	C9—C10	1.386 (2)
N3—C1	1.3624 (19)	C10—C11	1.367 (2)
N3—C17	1.433 (2)	C10—H10	0.93
N3—C16	1.435 (2)	C11—C12	1.381 (2)
O1—C8	1.2252 (16)	C11—H11	0.93
O2—C12	1.3550 (17)	C12—C13	1.377 (2)
O2—C15	1.413 (2)	C13—C14	1.3784 (19)
C1—C2	1.394 (2)	C13—H13	0.93
C1—C6	1.397 (2)	C14—H14	0.93
C2—C3	1.366 (2)	C15—H15A	0.96
C2—H2	0.93	C15—H15B	0.96
C3—C4	1.385 (2)	C15—H15C	0.96
C3—H3	0.93	C16—H16A	0.96
C4—C5	1.383 (2)	C16—H16B	0.96
C4—C7	1.447 (2)	C16—H16C	0.96
C5—C6	1.370 (2)	C17—H17A	0.96
C5—H5	0.93	C17—H17B	0.96
C6—H6	0.93	C17—H17C	0.96

C7—N1—N2	114.15 (12)	C10—C9—C8	117.84 (12)
C8—N2—N1	120.33 (11)	C11—C10—C9	121.00 (13)
C8—N2—H2A	121.3 (13)	C11—C10—H10	119.5
N1—N2—H2A	118.2 (13)	C9—C10—H10	119.5
C1—N3—C17	120.98 (15)	C10—C11—C12	120.25 (14)
C1—N3—C16	121.12 (15)	C10—C11—H11	119.9
C17—N3—C16	117.75 (15)	C12—C11—H11	119.9
C12—O2—C15	117.78 (13)	O2—C12—C13	124.65 (14)
N3—C1—C2	121.39 (14)	O2—C12—C11	115.72 (13)
N3—C1—C6	121.65 (14)	C13—C12—C11	119.63 (13)
C2—C1—C6	116.96 (13)	C12—C13—C14	119.67 (13)
C3—C2—C1	121.31 (14)	C12—C13—H13	120.2
C3—C2—H2	119.3	C14—C13—H13	120.2
C1—C2—H2	119.3	C13—C14—C9	121.28 (13)
C2—C3—C4	121.90 (14)	C13—C14—H14	119.4
C2—C3—H3	119.0	C9—C14—H14	119.4
C4—C3—H3	119.0	O2—C15—H15A	109.5
C5—C4—C3	116.82 (13)	O2—C15—H15B	109.5
C5—C4—C7	120.51 (13)	H15A—C15—H15B	109.5
C3—C4—C7	122.66 (13)	O2—C15—H15C	109.5
C6—C5—C4	122.15 (15)	H15A—C15—H15C	109.5
C6—C5—H5	118.9	H15B—C15—H15C	109.5
C4—C5—H5	118.9	N3—C16—H16A	109.5
C5—C6—C1	120.82 (15)	N3—C16—H16B	109.5
C5—C6—H6	119.6	H16A—C16—H16B	109.5
C1—C6—H6	119.6	N3—C16—H16C	109.5
N1—C7—C4	122.33 (13)	H16A—C16—H16C	109.5
N1—C7—H7	118.8	H16B—C16—H16C	109.5
C4—C7—H7	118.8	N3—C17—H17A	109.5
O1—C8—N2	123.01 (13)	N3—C17—H17B	109.5
O1—C8—C9	121.27 (12)	H17A—C17—H17B	109.5
N2—C8—C9	115.72 (11)	N3—C17—H17C	109.5
C14—C9—C10	118.16 (13)	H17A—C17—H17C	109.5
C14—C9—C8	124.00 (12)	H17B—C17—H17C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₂
M_r	297.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.922 (4), 13.224 (5), 9.756 (4)
β (°)	91.469 (6)
V (Å³)	1537.6 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.23 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.981, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	8744, 3296, 2507
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.03
No. of reflections	3296
No. of parameters	205
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+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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