N-[4-(Dimethyl­amino)benzyl­idene]-4-ethoxy­aniline

Wang, Q.; Wang, D.-Q.

doi:10.1107/S1600536807062277

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o51

https://doi.org/10.1107/S1600536807062277

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N-[4-(Dimethylamino)benzylidene]-4-ethoxyaniline

Qiang Wang ^a ^* and Da-Qi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: wdq4899@163.com

(Received 20 November 2007; accepted 22 November 2007; online 6 December 2007)

In the title compound, C₁₇H₂₀N₂O, the molecular core is planar, with a central C—N=C—C torsion angle of −179.3 (3)°. However, the overall geometry is not planar, with a dihedral angle of 61.96 (1)° between the two benzene rings, which adopt a trans configuration with respect to the C=N bond [1.269 (4) Å]. The bond lengths and angles are within normal ranges

Related literature

For biological activities, see: Yang et al. (2000 ). For related synthesis, see: Mondal et al. (2001 ); Tarafder et al. (2002 ).

Experimental

Crystal data

C₁₇H₂₀N₂O
M_r = 268.35
Monoclinic, P 2₁ /c
a = 9.586 (3) Å
b = 16.678 (7) Å
c = 9.722 (3) Å
β = 109.319 (4)°
V = 1466.7 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.34 × 0.27 × 0.19 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.97, T_max = 0.99
7422 measured reflections
2589 independent reflections
1323 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.164
S = 1.02
2589 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062277/bg2150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062277/bg2150Isup2.hkl

checkCIF report

Comment top

Schiff bases have been intensively investigated recently owing to their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities etc. (Yang et al., 2000; Mondal et al., 2001; Tarafder et al., 2002). We report here the synthesis and crystal structure of the title new Schiff base C₁₇H₂₀N₂O, (I).

The molecular structure of (I) is shown in Fig. 1. The molecular core is planar, with a central C—N?C—C torsion angle of -179.3 (3)°. The overall geometry instead, is not, with a dihedral angle of 61.96 (1)° between the two benzene rings, which adopt a trans configuration with respect to the C?N bond [1.269 (4) Å]. The bond lengths and angles are within normal ranges.

Related literature top

For biological activities, see: Yang et al. (2000). For related synthesis, see: Mondal et al. (2001); Tarafder et al. (2002).

Experimental top

P-dimethylamino benzaldehyde (5 mmol, 746.0 mg) in absolute ethanol (15 ml) was added dropwise to a absolute ethanol solution (5 ml) of p-ethoxyaniline (5 mmol, 685.9 mg). The mixture was heated under reflux with stirring for 3 h and then filtered. The resulting clear solution was kept at room temperature for 10 days, after which large pale-yellow block-shaped crystals of the title compound suitable for X-ray diffraction analysis were obtained.

Structure description top

For biological activities, see: Yang et al. (2000). For related synthesis, see: Mondal et al. (2001); Tarafder et al. (2002).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. A molecular view of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N-[4-(Dimethylamino)benzylidene]-4-ethoxyaniline top

Crystal data top

C₁₇H₂₀N₂O	F(000) = 576
M_r = 268.35	D_x = 1.215 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1506 reflections
a = 9.586 (3) Å	θ = 2.3–23.3°
b = 16.678 (7) Å	µ = 0.08 mm⁻¹
c = 9.722 (3) Å	T = 298 K
β = 109.319 (4)°	Block, light yellow
V = 1466.7 (9) Å³	0.34 × 0.27 × 0.19 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2589 independent reflections
Radiation source: fine-focus sealed tube	1323 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.97, T_max = 0.99	k = −19→15
7422 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0571P)² + 0.7834P] where P = (F_o² + 2F_c²)/3
2589 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O	V = 1466.7 (9) Å³
M_r = 268.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.586 (3) Å	µ = 0.08 mm⁻¹
b = 16.678 (7) Å	T = 298 K
c = 9.722 (3) Å	0.34 × 0.27 × 0.19 mm
β = 109.319 (4)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2589 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1323 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.99	R_int = 0.036
7422 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
2589 reflections	Δρ_min = −0.14 e Å⁻³
184 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

	x	y	z	U_iso*/U_eq
N1	0.5988 (3)	0.11288 (15)	0.4352 (3)	0.0543 (7)
N2	0.2098 (3)	0.13050 (17)	−0.2456 (3)	0.0614 (8)
O1	0.8309 (2)	0.13646 (13)	1.0402 (2)	0.0614 (6)
C1	0.4827 (3)	0.15105 (18)	0.3643 (4)	0.0521 (8)
H1	0.4384	0.1832	0.4163	0.063*
C2	0.4153 (3)	0.14752 (18)	0.2077 (3)	0.0479 (8)
C3	0.2738 (3)	0.17601 (19)	0.1395 (4)	0.0567 (9)
H3	0.2237	0.1999	0.1960	0.068*
C4	0.2044 (3)	0.17042 (19)	−0.0081 (4)	0.0566 (9)
H4	0.1082	0.1893	−0.0488	0.068*
C5	0.2761 (3)	0.13677 (18)	−0.0982 (4)	0.0493 (8)
C6	0.4203 (3)	0.10872 (19)	−0.0297 (4)	0.0547 (8)
H6	0.4723	0.0863	−0.0858	0.066*
C7	0.4858 (3)	0.11380 (19)	0.1179 (4)	0.0559 (9)
H7	0.5811	0.0939	0.1598	0.067*
C8	0.0542 (4)	0.1494 (2)	−0.3144 (4)	0.0716 (11)
H8A	−0.0036	0.1185	−0.2696	0.107*
H8B	0.0248	0.1368	−0.4163	0.107*
H8C	0.0386	0.2055	−0.3026	0.107*
C9	0.2890 (4)	0.1011 (2)	−0.3392 (4)	0.0782 (11)
H9A	0.3837	0.1269	−0.3137	0.117*
H9B	0.2332	0.1127	−0.4390	0.117*
H9C	0.3026	0.0442	−0.3268	0.117*
C10	0.6552 (3)	0.11975 (18)	0.5892 (3)	0.0475 (8)
C11	0.6938 (3)	0.05080 (19)	0.6712 (4)	0.0509 (8)
H11	0.6818	0.0013	0.6245	0.061*
C12	0.7501 (3)	0.05387 (19)	0.8218 (4)	0.0515 (8)
H12	0.7724	0.0066	0.8755	0.062*
C13	0.7731 (3)	0.12667 (18)	0.8921 (3)	0.0485 (8)
C14	0.7365 (3)	0.19622 (19)	0.8103 (4)	0.0542 (8)
H14	0.7519	0.2457	0.8570	0.065*
C15	0.6778 (3)	0.19303 (19)	0.6611 (4)	0.0554 (9)
H15	0.6531	0.2403	0.6077	0.066*
C16	0.8842 (4)	0.0675 (2)	1.1264 (3)	0.0629 (9)
H16A	0.9620	0.0425	1.0981	0.075*
H16B	0.8049	0.0290	1.1124	0.075*
C17	0.9428 (4)	0.0927 (2)	1.2824 (4)	0.0781 (11)
H17A	1.0181	0.1325	1.2944	0.117*
H17B	0.9841	0.0470	1.3421	0.117*
H17C	0.8639	0.1146	1.3109	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0525 (16)	0.0502 (17)	0.0639 (18)	0.0000 (14)	0.0244 (14)	−0.0015 (14)
N2	0.0514 (16)	0.075 (2)	0.0631 (18)	0.0029 (14)	0.0266 (14)	−0.0008 (16)
O1	0.0751 (15)	0.0487 (14)	0.0638 (15)	0.0040 (11)	0.0275 (12)	−0.0021 (12)
C1	0.0502 (19)	0.0427 (19)	0.070 (2)	−0.0031 (15)	0.0294 (17)	−0.0041 (16)
C2	0.0479 (18)	0.0387 (18)	0.061 (2)	−0.0032 (14)	0.0239 (16)	−0.0009 (15)
C3	0.052 (2)	0.054 (2)	0.071 (2)	0.0082 (16)	0.0306 (18)	−0.0053 (17)
C4	0.0463 (18)	0.055 (2)	0.073 (2)	0.0083 (16)	0.0253 (17)	0.0002 (18)
C5	0.0455 (18)	0.0440 (19)	0.066 (2)	−0.0046 (14)	0.0281 (16)	0.0000 (16)
C6	0.0495 (19)	0.055 (2)	0.069 (2)	−0.0002 (15)	0.0317 (17)	−0.0051 (17)
C7	0.0392 (17)	0.053 (2)	0.079 (3)	0.0021 (15)	0.0237 (17)	−0.0010 (18)
C8	0.056 (2)	0.087 (3)	0.072 (2)	−0.0053 (19)	0.0212 (18)	0.000 (2)
C9	0.075 (2)	0.097 (3)	0.074 (2)	0.009 (2)	0.039 (2)	0.001 (2)
C10	0.0418 (17)	0.047 (2)	0.060 (2)	−0.0020 (14)	0.0245 (15)	−0.0031 (17)
C11	0.0505 (19)	0.0389 (19)	0.066 (2)	−0.0018 (14)	0.0235 (16)	−0.0057 (16)
C12	0.0498 (19)	0.0391 (19)	0.069 (2)	0.0011 (14)	0.0250 (17)	0.0032 (17)
C13	0.0462 (18)	0.045 (2)	0.061 (2)	0.0013 (15)	0.0273 (15)	−0.0017 (17)
C14	0.063 (2)	0.0372 (19)	0.071 (2)	−0.0010 (15)	0.0330 (18)	−0.0045 (17)
C15	0.062 (2)	0.042 (2)	0.071 (2)	0.0049 (15)	0.0325 (18)	0.0033 (17)
C16	0.066 (2)	0.061 (2)	0.063 (2)	0.0080 (18)	0.0234 (18)	0.0030 (19)
C17	0.085 (3)	0.082 (3)	0.063 (2)	0.004 (2)	0.018 (2)	0.000 (2)

Geometric parameters (Å, º) top

N1—C1	1.269 (4)	C8—H8C	0.9600
N1—C10	1.418 (4)	C9—H9A	0.9600
N2—C5	1.366 (4)	C9—H9B	0.9600
N2—C9	1.450 (4)	C9—H9C	0.9600
N2—C8	1.453 (4)	C10—C11	1.378 (4)
O1—C13	1.370 (4)	C10—C15	1.389 (4)
O1—C16	1.415 (4)	C11—C12	1.384 (4)
C1—C2	1.445 (4)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.375 (4)
C2—C3	1.383 (4)	C12—H12	0.9300
C2—C7	1.387 (4)	C13—C14	1.385 (4)
C3—C4	1.370 (4)	C14—C15	1.372 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.398 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.492 (4)
C5—C6	1.402 (4)	C16—H16A	0.9700
C6—C7	1.366 (4)	C16—H16B	0.9700
C6—H6	0.9300	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—H8A	0.9600	C17—H17C	0.9600
C8—H8B	0.9600

C1—N1—C10	119.5 (3)	H9A—C9—H9B	109.5
C5—N2—C9	121.7 (3)	N2—C9—H9C	109.5
C5—N2—C8	121.1 (3)	H9A—C9—H9C	109.5
C9—N2—C8	117.1 (3)	H9B—C9—H9C	109.5
C13—O1—C16	117.8 (2)	C11—C10—C15	118.4 (3)
N1—C1—C2	123.9 (3)	C11—C10—N1	118.6 (3)
N1—C1—H1	118.0	C15—C10—N1	122.9 (3)
C2—C1—H1	118.0	C10—C11—C12	121.2 (3)
C3—C2—C7	116.2 (3)	C10—C11—H11	119.4
C3—C2—C1	121.1 (3)	C12—C11—H11	119.4
C7—C2—C1	122.6 (3)	C13—C12—C11	120.1 (3)
C4—C3—C2	122.6 (3)	C13—C12—H12	120.0
C4—C3—H3	118.7	C11—C12—H12	120.0
C2—C3—H3	118.7	O1—C13—C12	124.8 (3)
C3—C4—C5	121.0 (3)	O1—C13—C14	116.2 (3)
C3—C4—H4	119.5	C12—C13—C14	119.0 (3)
C5—C4—H4	119.5	C15—C14—C13	120.8 (3)
N2—C5—C4	122.3 (3)	C15—C14—H14	119.6
N2—C5—C6	121.1 (3)	C13—C14—H14	119.6
C4—C5—C6	116.7 (3)	C14—C15—C10	120.5 (3)
C7—C6—C5	121.1 (3)	C14—C15—H15	119.8
C7—C6—H6	119.4	C10—C15—H15	119.8
C5—C6—H6	119.4	O1—C16—C17	108.3 (3)
C6—C7—C2	122.4 (3)	O1—C16—H16A	110.0
C6—C7—H7	118.8	C17—C16—H16A	110.0
C2—C7—H7	118.8	O1—C16—H16B	110.0
N2—C8—H8A	109.5	C17—C16—H16B	110.0
N2—C8—H8B	109.5	H16A—C16—H16B	108.4
H8A—C8—H8B	109.5	C16—C17—H17A	109.5
N2—C8—H8C	109.5	C16—C17—H17B	109.5
H8A—C8—H8C	109.5	H17A—C17—H17B	109.5
H8B—C8—H8C	109.5	C16—C17—H17C	109.5
N2—C9—H9A	109.5	H17A—C17—H17C	109.5
N2—C9—H9B	109.5	H17B—C17—H17C	109.5

C10—N1—C1—C2	−179.3 (3)	C1—C2—C7—C6	178.3 (3)
N1—C1—C2—C3	166.0 (3)	C1—N1—C10—C11	132.5 (3)
N1—C1—C2—C7	−12.1 (5)	C1—N1—C10—C15	−49.7 (4)
C7—C2—C3—C4	1.2 (5)	C15—C10—C11—C12	1.7 (4)
C1—C2—C3—C4	−177.1 (3)	N1—C10—C11—C12	179.7 (3)
C2—C3—C4—C5	−1.5 (5)	C10—C11—C12—C13	−2.2 (4)
C9—N2—C5—C4	175.3 (3)	C16—O1—C13—C12	6.5 (4)
C8—N2—C5—C4	−7.8 (5)	C16—O1—C13—C14	−173.4 (3)
C9—N2—C5—C6	−5.3 (5)	C11—C12—C13—O1	−178.6 (3)
C8—N2—C5—C6	171.6 (3)	C11—C12—C13—C14	1.2 (4)
C3—C4—C5—N2	−179.9 (3)	O1—C13—C14—C15	180.0 (3)
C3—C4—C5—C6	0.7 (5)	C12—C13—C14—C15	0.1 (4)
N2—C5—C6—C7	−178.9 (3)	C13—C14—C15—C10	−0.6 (4)
C4—C5—C6—C7	0.5 (5)	C11—C10—C15—C14	−0.4 (4)
C5—C6—C7—C2	−0.9 (5)	N1—C10—C15—C14	−178.2 (3)
C3—C2—C7—C6	0.0 (5)	C13—O1—C16—C17	179.4 (3)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O
M_r	268.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.586 (3), 16.678 (7), 9.722 (3)
β (°)	109.319 (4)
V (Å³)	1466.7 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.27 × 0.19

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.97, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	7422, 2589, 1323
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.164, 1.02
No. of reflections	2589
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Acknowledgements

The authors acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, People's Republic of China.

References

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