N-Benzyl-N-[(E)-(3,4,5-trimethoxy­phen­yl)methyl­idene]amine

Santacruz, L.; Abonia, R.; Low, J.N.; Cobo, J.

doi:10.1107/S1600536806040785

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 11| November 2006| Pages o5027-o5028

https://doi.org/10.1107/S1600536806040785

N-Benzyl-N-[(E)-(3,4,5-trimethoxyphenyl)methylidene]amine

Lynay Santacruz,^a Rodrigo Abonia,^a John Nicolson Low ^b ^* and Justo Cobo ^c

^aGrupo de Investigacíon Heterocíclicos, Deparatmento de Química, Universidad de Valle, A.A. 25360 Cali, Colombia, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland, and ^cDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 - Jaén, Spain
^*Correspondence e-mail: che562@abdn.ac.uk

(Received 2 October 2006; accepted 3 October 2006; online 18 October 2006)

In the title molecule, C₁₇H₁₉NO₃, the dihedral angle formed by the planes of the two benzene rings is 62.3 (1)°. There are no direction-specific interactions in the supramolecular structure.

Comment

The bond lengths and angles in the title compound, (I), show no unusual features. The central part of the molecule is essentially planar, with only the methyl group at C241 and the phenyl group attached to atom C1 tilted out of the plane. This is shown by the leading torsion angles given in Table 1. The dihedral angle formed by the planes of the two benzene rings is 62.3 (1)°.

Figure 1
Molecular structure of (I)

with the numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Experimental

A neat mixture of benzylamine (3.17 mmol) and 3,4,5-trimethoxybenzaldehyde (3.11 mmol) was heated at 373 K for five minutes. After cooling, a white solid was obtained in quantitative yield. Crystals suitable for single-crystal X-ray diffraction were grown from ethanol (m.p. 367 K).

Crystal data

C₁₇H₁₉NO₃
M_r = 285.33
Monoclinic, P 2₁ /c
a = 22.1302 (10) Å
b = 5.3140 (2) Å
c = 12.4571 (5) Å
β = 98.447 (2)°
V = 1449.06 (10) Å³
Z = 4
D_x = 1.308 Mg m⁻³
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 (2) K
Plate, colourless
0.42 × 0.34 × 0.03 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.963, T_max = 0.997
14669 measured reflections
3317 independent reflections
2627 reflections with I > 2σ(I)
R_int = 0.055
θ_max = 27.6°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.154
S = 1.14
3317 reflections
193 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0543P)² + 1.1271P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected torsion angles (°)

C2—N1—C1—C11	125.0 (2)
C1—N1—C2—C21	175.79 (18)
N1—C1—C11—C16	89.1 (2)
N1—C1—C11—C12	−91.1 (2)
N1—C2—C21—C26	172.26 (19)
N1—C2—C21—C22	−9.6 (3)
C22—C23—O23—C231	3.5 (3)
C24—C23—O23—C231	−176.53 (16)
C25—C24—O24—C241	72.8 (2)
C23—C24—O24—C241	−110.4 (2)
C26—C25—O25—C251	3.7 (3)
C24—C25—O25—C251	−176.98 (17)

H atoms were treated as riding, with C—H = 0.95, 0.99 and 0.98 Å for aromatic, methylene and methyl C, respectively; U_iso(H) = xU_eq(C), where x = 1.5 for methyl and 1.2 for other H atoms.

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97; molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806040785/lh2199sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806040785/lh2199Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL & SHELXL97; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

N-benzyl-N-[(E)-(3,4,5-trimethoxyphenyl)methylidene]amine top

Crystal data top

C₁₇H₁₉NO₃	F(000) = 608
M_r = 285.33	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 367 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 22.1302 (10) Å	Cell parameters from 3317 reflections
b = 5.3140 (2) Å	θ = 3.3–27.6°
c = 12.4571 (5) Å	µ = 0.09 mm⁻¹
β = 98.447 (2)°	T = 120 K
V = 1449.06 (10) Å³	Plate, colourless
Z = 4	0.42 × 0.34 × 0.03 mm

Data collection top

Bruker-Nonius KappaCCD diffractometer	3317 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.3°
φ & ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −6→6
T_min = 0.963, T_max = 0.997	l = −16→16
14669 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0543P)² + 1.1271P] where P = (F_o² + 2F_c²)/3
3317 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

MS (IE 70 eV): m/z (%) 285 (45), 270 (6), 254 (5), 91 (100).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.17303 (7)	0.3758 (3)	0.49211 (13)	0.0216 (4)
C1	0.12212 (9)	0.2916 (4)	0.54614 (17)	0.0243 (4)
C2	0.21935 (9)	0.2331 (4)	0.50281 (15)	0.0201 (4)
C11	0.10308 (8)	0.4877 (4)	0.62221 (16)	0.0210 (4)
C12	0.12924 (9)	0.4898 (4)	0.73129 (17)	0.0264 (5)
C13	0.11283 (10)	0.6721 (4)	0.80159 (18)	0.0298 (5)
C14	0.06916 (10)	0.8502 (4)	0.76425 (19)	0.0297 (5)
C15	0.04209 (10)	0.8478 (4)	0.65706 (19)	0.0277 (5)
C16	0.05928 (9)	0.6690 (4)	0.58604 (17)	0.0241 (4)
C21	0.27357 (8)	0.2747 (4)	0.44917 (15)	0.0187 (4)
C22	0.27406 (8)	0.4577 (4)	0.36889 (15)	0.0183 (4)
C23	0.32533 (9)	0.4804 (4)	0.31665 (15)	0.0181 (4)
O23	0.33080 (6)	0.6491 (3)	0.23613 (11)	0.0216 (3)
C231	0.28149 (9)	0.8224 (4)	0.20817 (17)	0.0228 (4)
C24	0.37622 (8)	0.3231 (4)	0.34585 (15)	0.0179 (4)
O24	0.42718 (6)	0.3559 (3)	0.29596 (11)	0.0211 (3)
C241	0.43719 (9)	0.1529 (4)	0.22369 (17)	0.0244 (4)
C25	0.37572 (8)	0.1454 (4)	0.42831 (15)	0.0186 (4)
O25	0.42793 (6)	0.0090 (3)	0.45386 (11)	0.0241 (3)
C251	0.42837 (9)	−0.1839 (4)	0.53421 (17)	0.0235 (4)
C26	0.32410 (9)	0.1194 (4)	0.47905 (15)	0.0201 (4)
H1A	0.1342	0.1361	0.5876	0.029*
H1B	0.0868	0.2504	0.4905	0.029*
H2	0.2191	0.0899	0.5484	0.024*
H12	0.1585	0.3654	0.7577	0.032*
H13	0.1316	0.6745	0.8752	0.036*
H14	0.0578	0.9743	0.8124	0.036*
H15	0.0117	0.9687	0.6318	0.033*
H16	0.0410	0.6702	0.5121	0.029*
H22	0.2399	0.5653	0.3501	0.022*
H23A	0.2757	0.9214	0.2723	0.034*
H23B	0.2440	0.7292	0.1823	0.034*
H23C	0.2910	0.9354	0.1508	0.034*
H24A	0.4049	0.1541	0.1608	0.037*
H24B	0.4365	−0.0079	0.2620	0.037*
H24C	0.4770	0.1747	0.1992	0.037*
H25A	0.3958	−0.3053	0.5107	0.035*
H25B	0.4217	−0.1082	0.6033	0.035*
H25C	0.4679	−0.2702	0.5437	0.035*
H26	0.3233	−0.0040	0.5340	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0199 (8)	0.0253 (9)	0.0207 (8)	−0.0002 (7)	0.0066 (6)	−0.0010 (7)
C1	0.0197 (9)	0.0266 (11)	0.0281 (11)	−0.0033 (8)	0.0092 (8)	−0.0024 (9)
C2	0.0219 (10)	0.0207 (10)	0.0183 (9)	−0.0010 (8)	0.0045 (7)	0.0008 (8)
C11	0.0158 (9)	0.0226 (10)	0.0259 (10)	−0.0043 (7)	0.0070 (7)	−0.0001 (8)
C12	0.0211 (10)	0.0291 (12)	0.0293 (11)	−0.0012 (8)	0.0049 (8)	0.0008 (9)
C13	0.0307 (11)	0.0354 (13)	0.0240 (11)	−0.0077 (9)	0.0068 (9)	−0.0029 (9)
C14	0.0338 (12)	0.0250 (11)	0.0341 (12)	−0.0054 (9)	0.0174 (9)	−0.0038 (9)
C15	0.0235 (10)	0.0231 (11)	0.0385 (12)	0.0000 (8)	0.0118 (9)	0.0027 (9)
C16	0.0213 (9)	0.0247 (11)	0.0268 (10)	−0.0044 (8)	0.0053 (8)	0.0028 (8)
C21	0.0192 (9)	0.0200 (10)	0.0171 (9)	−0.0016 (7)	0.0039 (7)	−0.0041 (8)
C22	0.0175 (9)	0.0189 (9)	0.0184 (9)	0.0018 (7)	0.0018 (7)	−0.0018 (8)
C23	0.0210 (9)	0.0168 (9)	0.0166 (9)	−0.0014 (7)	0.0032 (7)	−0.0017 (7)
O23	0.0212 (7)	0.0220 (7)	0.0229 (7)	0.0033 (5)	0.0072 (5)	0.0049 (6)
C231	0.0240 (10)	0.0206 (10)	0.0237 (10)	0.0039 (8)	0.0035 (8)	0.0032 (8)
C24	0.0154 (9)	0.0204 (10)	0.0185 (9)	−0.0024 (7)	0.0043 (7)	−0.0022 (8)
O24	0.0174 (7)	0.0218 (7)	0.0257 (7)	−0.0015 (5)	0.0084 (5)	−0.0016 (6)
C241	0.0235 (10)	0.0245 (11)	0.0271 (10)	0.0027 (8)	0.0099 (8)	−0.0022 (9)
C25	0.0156 (9)	0.0196 (10)	0.0197 (9)	0.0013 (7)	−0.0003 (7)	−0.0021 (8)
O25	0.0170 (7)	0.0289 (8)	0.0265 (7)	0.0051 (6)	0.0033 (5)	0.0078 (6)
C251	0.0223 (10)	0.0228 (10)	0.0244 (10)	0.0026 (8)	−0.0003 (8)	0.0041 (8)
C26	0.0202 (9)	0.0211 (10)	0.0189 (9)	−0.0003 (7)	0.0029 (7)	0.0019 (8)

Geometric parameters (Å, º) top

N1—C2	1.266 (3)	C22—H22	0.95
N1—C1	1.465 (2)	C23—O23	1.364 (2)
C1—C11	1.510 (3)	C23—C24	1.407 (3)
C1—H1A	0.99	O23—C231	1.431 (2)
C1—H1B	0.99	C231—H23A	0.98
C2—C21	1.473 (3)	C231—H23B	0.98
C2—H2	0.95	C231—H23C	0.98
C11—C16	1.394 (3)	C24—O24	1.376 (2)
C11—C12	1.397 (3)	C24—C25	1.397 (3)
C12—C13	1.390 (3)	O24—C241	1.443 (2)
C12—H12	0.95	C241—H24A	0.98
C13—C14	1.384 (3)	C241—H24B	0.98
C13—H13	0.95	C241—H24C	0.98
C14—C15	1.381 (3)	C25—O25	1.361 (2)
C14—H14	0.95	C25—C26	1.391 (3)
C15—C16	1.389 (3)	O25—C251	1.432 (2)
C15—H15	0.95	C251—H25A	0.98
C16—H16	0.95	C251—H25B	0.98
C21—C26	1.395 (3)	C251—H25C	0.98
C21—C22	1.396 (3)	C26—H26	0.95
C22—C23	1.394 (3)

C2—N1—C1	115.73 (17)	O23—C23—C22	124.54 (17)
N1—C1—C11	112.45 (17)	O23—C23—C24	115.24 (16)
N1—C1—H1A	109.1	C22—C23—C24	120.23 (17)
C11—C1—H1A	109.1	C23—O23—C231	117.07 (14)
N1—C1—H1B	109.1	O23—C231—H23A	109.5
C11—C1—H1B	109.1	O23—C231—H23B	109.5
H1A—C1—H1B	107.8	H23A—C231—H23B	109.5
N1—C2—C21	124.27 (18)	O23—C231—H23C	109.5
N1—C2—H2	117.9	H23A—C231—H23C	109.5
C21—C2—H2	117.9	H23B—C231—H23C	109.5
C16—C11—C12	118.58 (19)	O24—C24—C25	120.88 (17)
C16—C11—C1	121.29 (18)	O24—C24—C23	119.08 (17)
C12—C11—C1	120.14 (19)	C25—C24—C23	119.96 (16)
C13—C12—C11	120.6 (2)	C24—O24—C241	113.47 (15)
C13—C12—H12	119.7	O24—C241—H24A	109.5
C11—C12—H12	119.7	O24—C241—H24B	109.5
C14—C13—C12	120.0 (2)	H24A—C241—H24B	109.5
C14—C13—H13	120.0	O24—C241—H24C	109.5
C12—C13—H13	120.0	H24A—C241—H24C	109.5
C15—C14—C13	120.1 (2)	H24B—C241—H24C	109.5
C15—C14—H14	120.0	O25—C25—C26	124.48 (17)
C13—C14—H14	120.0	O25—C25—C24	115.71 (16)
C14—C15—C16	120.1 (2)	C26—C25—C24	119.81 (17)
C14—C15—H15	119.9	C25—O25—C251	117.58 (15)
C16—C15—H15	119.9	O25—C251—H25A	109.5
C15—C16—C11	120.6 (2)	O25—C251—H25B	109.5
C15—C16—H16	119.7	H25A—C251—H25B	109.5
C11—C16—H16	119.7	O25—C251—H25C	109.5
C26—C21—C22	120.85 (17)	H25A—C251—H25C	109.5
C26—C21—C2	117.68 (17)	H25B—C251—H25C	109.5
C22—C21—C2	121.45 (17)	C25—C26—C21	119.95 (18)
C23—C22—C21	119.17 (17)	C25—C26—H26	120.0
C23—C22—H22	120.4	C21—C26—H26	120.0
C21—C22—H22	120.4

C2—N1—C1—C11	125.0 (2)	C22—C23—O23—C231	3.5 (3)
C1—N1—C2—C21	175.79 (18)	C24—C23—O23—C231	−176.53 (16)
N1—C1—C11—C16	89.1 (2)	O23—C23—C24—O24	2.5 (3)
N1—C1—C11—C12	−91.1 (2)	C22—C23—C24—O24	−177.52 (17)
C16—C11—C12—C13	−1.4 (3)	O23—C23—C24—C25	179.29 (17)
C1—C11—C12—C13	178.87 (18)	C22—C23—C24—C25	−0.8 (3)
C11—C12—C13—C14	1.5 (3)	C25—C24—O24—C241	72.8 (2)
C12—C13—C14—C15	−0.4 (3)	C23—C24—O24—C241	−110.4 (2)
C13—C14—C15—C16	−1.0 (3)	O24—C24—C25—O25	−0.7 (3)
C14—C15—C16—C11	1.1 (3)	C23—C24—C25—O25	−177.41 (17)
C12—C11—C16—C15	0.0 (3)	O24—C24—C25—C26	178.67 (17)
C1—C11—C16—C15	179.81 (18)	C23—C24—C25—C26	2.0 (3)
N1—C2—C21—C26	172.26 (19)	C26—C25—O25—C251	3.7 (3)
N1—C2—C21—C22	−9.6 (3)	C24—C25—O25—C251	−176.98 (17)
C26—C21—C22—C23	1.5 (3)	O25—C25—C26—C21	177.84 (18)
C2—C21—C22—C23	−176.64 (17)	C24—C25—C26—C21	−1.5 (3)
C21—C22—C23—O23	179.02 (17)	C22—C21—C26—C25	−0.2 (3)
C21—C22—C23—C24	−0.9 (3)	C2—C21—C26—C25	177.91 (17)

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. The authors thank the staff for all their help and advice. JC thanks the Consejería de Innovacíon, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. RA and LS thank COLCIENCIAS, UNIVALLE (Universidad del Valle, Colombia), and RA also thanks AUIP for supporting a research fellowship.

References

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